Professor Iain Coldham
School of Mathematical and Physical Sciences
Professor of Synthetic Organic Chemistry
i.coldham@sheffield.ac.uk
+44 114 222 9428
+44 114 222 9428
Dainton Building
Full contact details
Professor Iain Coldham
School of Mathematical and Physical Sciences
Dainton Building
13 Brook Hill
Sheffield
S3 7HF
School of Mathematical and Physical Sciences
Dainton Building
13 Brook Hill
Sheffield
S3 7HF
- Profile
-
Professor Coldham obtained a BA in Chemistry from the University of Cambridge in 1986, followed by a PhD in 1989. After a postdoctoral research fellowship at the University of Texas at Austin (1989-1991), he was a member of staff at the University of Exeter as a Lecturer/Senior Lecturer from 1991 to 2003. In 2003 he became a Reader at the University of Sheffield, where he was promoted to Professor of Synthetic Organic Chemistry in 2008.
- Research interests
-
New methodology in organic chemistry
Synthetic chemistry depends on reliable, high-yielding and selective reactions that access a wide variety of different structures. The discovery of new methods in synthesis is crucial to expand the range of novel compounds that can be made easily. Especially important is the development of new carbon-carbon bond-forming reactions. Our research group is studying the use of organometallic compounds in asymmetric synthesis, especially for carbon-carbon bond formation of nitrogen-containing compounds, prevalent in many biologically active molecules.
We have found that 2-lithiopyrrolidines, piperidines and other cyclic amines undergo dynamic resolution in the presence of a chiral ligand (L*), leading to highly enantioenriched 2-substituted cyclic amine products. We have determined the kinetics of enantiomerization of several chiral organolithium compounds.
Synthesis of biologically active compounds
We are using dipolar cycloaddition chemistry to access a variety of alkaloid structures. Intramolecular cycloadditions provide an efficient means to build up bicyclic and polycyclic ring systems in a rapid and stereocontrolled way.
We have shown that this chemistry is applicable to the synthesis of the core ring system of the alkaloid manzamine A, which has significant biological activity (anti-cancer, anti-malarial, and other activity). One dipole that we use is an azomethine ylide, that we make by condensation of a secondary amine with an aldehyde. Intramolecular cycloaddition sets up two new rings and up to four new stereocentres in a single step. We have prepared simpler analogues of manzamine A and other heteroaromatic compounds to probe their biological activity.
Recently, we have found that primary amines (such as amino-acids, amino-esters, hydroxylamine) can be used to condense with an aldehyde and promote a cascade process involving imine formation, cyclization, ylide formation and cycloaddition all in one pot. This chemistry provides an efficient method to prepare three rings directly from an acyclic aldehyde in a stereocontrolled way and has been applied to the total syntheses of several alkaloids (such as aspidospermidine, aspidospermine, quebrachamine and myrioxazine A).
- Publications
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Books
- Applications of Domino Transformations in Organic Synthesis 2. Georg Thieme Verlag KG.
Journal articles
- New benzotriazole-derived α-substituted hemiaminal ethers with enhanced cholinesterase inhibition activity: Synthesis, structural, and biological evaluations. Journal of Saudi Chemical Society, 27(6), 101746-101746.
- Kinetic resolution of 2‐aryldihydroquinolines using lithiation – synthesis of chiral 1,2‐ and 1,4‐dihydroquinolines. Chemistry – A European Journal.
- Photocatalysis and kinetic resolution by lithiation to give enantioenriched 2-arylpiperazines. Organic Letters, 25(6), 987-991.
- Kinetic Resolution of 2-Aryl-4-methylenepiperidines toward Enantioenriched Functionalizable Piperidine Fragments.. J Org Chem.
- Kinetic resolution by lithiation: highly enantioselective synthesis of substituted dihydrobenzoxazines and tetrahydroquinoxalines. Synthesis. View this article in WRRO
- Asymmetric synthesis of 2-arylindolines and 2,2-disubstituted indolines by kinetic resolution.. Chemistry - A European Journal. View this article in WRRO
- Splicing factor YBX1 mediates persistence of JAK2-mutated neoplasms. Nature, 588(7836), 157-163.
- Stuart Warren (24 Dec 1938–22 Mar 2020). Organic & Biomolecular Chemistry, 18(37), 7236-7237.
- Synthesis of spirocyclic amines by 1,3-dipolar cycloaddition of azomethine ylides and azomethine imines. Synthesis. View this article in WRRO
- Three-component couplings for the synthesis of pyrroloquinoxalinones by azomethine ylide 1,3-dipolar cycloaddition chemistry. Tetrahedron Letters, 60(37). View this article in WRRO
- Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts. Beilstein Journal of Organic Chemistry, 15, 1480-1484. View this article in WRRO
- Regioselective lithiation and electrophilic quench of N‐Boc‐3‐phenyltetrahydroisoquinoline. European Journal of Organic Chemistry. View this article in WRRO
- Unfolded protein response is an early, non-critical event during hepatic stellate cell activation. Cell Death & Disease, 10(2). View this article in WRRO
- Cascade cyclization and intramolecular nitrone dipolar cycloaddition and formal synthesis of 19-hydroxyibogamine. Organic & Biomolecular Chemistry. View this article in WRRO
- Preparation of substituted tetrahydro-1-benzazepines by lithiation-trapping. European Journal of Organic Chemistry. View this article in WRRO
- Synthesis and kinetic resolution of substituted tetrahydroquinolines by lithiation then electrophilic quench. Chemical Science, 9(5), 1352-1357. View this article in WRRO
- Lithiation–Substitution of N-Boc-2-phenylazepane. Synlett. View this article in WRRO
- Synthesis of Spirocyclic Amines by Using Dipolar Cycloadditions of Nitrones. The Journal of Organic Chemistry, 82(12), 6489-6496. View this article in WRRO
- Highly Enantioselective Metalation-Substitution alpha to a Chiral Nitrile. SYNLETT, A80-A82. View this article in WRRO
- Metallation–substitution of an α-oxygenated chiral nitrile. Comptes Rendus Chimie. View this article in WRRO
- Cascade oxime formation, cyclization to a nitrone, and intermolecular dipolar cycloaddition. Org. Biomol. Chem.. View this article in WRRO
- Highly enantioselective metallation–substitution alpha to a chiral nitrile. Chemical Science, 8, 1436-1441. View this article in WRRO
- ChemInform Abstract: Synthesis of Substituted Tetrahydroisoquinolines by Lithiation Then Electrophilic Quench.. ChemInform, 47(40).
- Synthesis of substituted tetrahydroisoquinolines by lithiation then electrophilic quench. Org. Biomol. Chem., 14(21), 4908-4917. View this article in WRRO
- Synthesis and activity of a novel inhibitor of nonsense-mediated mRNA decay. Org. Biomol. Chem., 14(5), 1559-1563. View this article in WRRO
- ChemInform Abstract: Preparation of 1-Substituted Tetrahydro-β-carbolines by Lithiation-Substitution.. ChemInform, 46(43), no-no.
- Preparation of 1-Substituted Tetrahydro-β-carbolines by Lithiation–Substitution. The Journal of Organic Chemistry, 80(11), 5964-5969. View this article in WRRO
- ChemInform Abstract: Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines by Lithiation and Substitution, with in situ IR Spectroscopy and Configurational Stability Studies.. ChemInform, 45(42), no-no.
- Lithium Compounds in Organic Synthesis: From Fundamentals to Applications RenzoLuisi (Editor) and VitoCapriati (Editor) Wiley-VCH; April 2014 555 pages ISBN: 978-3-527-33343-1 576 pages Hardcover £130 E-book £104.99. Applied Organometallic Chemistry, 28(10), 800-800.
- Synthesis and kinetic resolution of N-Boc-2-arylpiperidines. Chemical Communications, 50(69), 9910-9913. View this article in WRRO
- ChemInform Abstract: Arylthio-Metal Exchange of α-Arylthioalkanenitriles.. ChemInform, 45(24), no-no.
- Synthesis of 1,1-disubstituted tetrahydroisoquinolines by lithiation and substitution, with in situ IR spectroscopy and configurational stability studies.. J Am Chem Soc, 136(15), 5551-5554. View this article in WRRO
- Synthesis of an azabicyclic framework towards (±)-actinophyllic acid. Tetrahedron Letters, 55(6), 1255-1257. View this article in WRRO
- Arylthio-metal exchange of α-arylthioalkanenitriles.. Org Lett, 16(1), 62-65.
- ChemInform Abstract: Remarkable Configurational Stability of Magnesiated Nitriles.. ChemInform, 44(49), no-no.
- ChemInform Abstract: Synthesis of 1-Substituted Tetrahydroisoquinolines by Lithiation and Electrophilic Quenching Guided by in situ IR and NMR Spectroscopy and Application to the Synthesis of Salsolidine, Carnegine and Laudanosine.. ChemInform, 44(45), no-no.
- Remarkable Configurational Stability of Magnesiated Nitriles. Angewandte Chemie, 125(30), 7854-7857.
- Remarkable configurational stability of magnesiated nitriles.. Angew Chem Int Ed Engl, 52(30), 7700-7703.
- Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine.. Chemistry, 19(24), 7724-7730.
- Intramolecular carbolithiation reactions in the construction of medium-sized rings. Synthesis of pyrroloisoquinolines, benzazepines, and benzazocines. European Journal of Organic Chemistry(8), 1460-1470.
- ChemInform Abstract: Asymmetric Synthesis of 2-Arylpyrrolidines by Cationic Cyclization.. ChemInform, 44(4), no-no.
- ChemInform Abstract: Synthesis of Fused Tricyclic Heterocycles by Condensation, Cyclization, Dipolar Cycloaddition Cascade of α-Benzenesulfonyl and α-Phenylthio Substituted Aldehydes.. ChemInform, 43(19), no-no.
- Selectivity in the aggregates of the chiral organolithium N-Boc-2-lithiopiperidine with a chiral ligand: A DFT study. Molecular Physics, 110(6), 353-359.
- An experimental and in situ IR spectroscopic study of the lithiation-substitution of N-Boc-2-phenylpyrrolidine and -piperidine: controlling the formation of quaternary stereocenters.. J Am Chem Soc, 134(11), 5300-5308.
- Synthesis and evaluation of 1-amino-6-halo-β-carbolines as antimalarial and antiprion agents.. ChemMedChem, 7(4), 578-586.
- Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy. Beilstein Journal of Organic Chemistry, 8, 107-111. View this article in WRRO
- Asymmetric synthesis of 2-arylpyrrolidines by cationic cyclization. Synlett, 23(16), 2405-2407.
- Cascade cyclization, dipolar cycloaddition of azomethine imines for the synthesis of pyrazolidines.. Org Biomol Chem, 9(22), 7921-7928.
- 2,4-diarylthiazole antiprion compounds as a novel structural class of antimalarial leads.. Bioorg Med Chem Lett, 21(12), 3644-3647.
- Synthesis of the core ring system of the yuzurimine-type Daphniphyllum alkaloids by cascade condensation, cyclization, cycloaddition chemistry.. J Org Chem, 76(7), 2360-2366.
- Cascade cyclization, dipolar cycloaddition to bridged tricyclic amines related to the Daphniphyllum alkaloids.. Org Lett, 13(6), 1267-1269.
- Transannular dipolar cycloaddition as an approach towards the synthesis of the core ring system of the sarain alkaloids.. Org Biomol Chem, 9(6), 1901-1907.
- ChemInform Abstract: Synthesis of Natural Products Using Intramolecular Dipolar Cycloaddition Reactions. ChemInform, 42(1), no-no.
- Synthesis of fused tricyclic heterocycles by condensation, cyclization, dipolar cycloaddition cascade of α-benzenesulfonyl and α-phenylthio substituted aldehydes. Heterocycles, 84(1), 597-613.
- Organolithium or Heck-type cyclization of N-ortho-iodobenzyl-2- alkenylpyrrolidines to give indolizidines. Arkivoc, 2011(5), 57-66.
- LITHIATION OF DEOXYPEGANINE AND CHIRAL SYNTHESIS OF DEOXYPEGANINE DERIVATIVES. CHEM NAT COMPD+, 46(6), 929-931.
- Lithiation of deoxypeganine and chiral synthesis of deoxypeganine derivatives. Chemistry of Natural Compounds, 1-3.
- ChemInform Abstract: Regioselective and Stereoselective Copper(I)-Promoted Allylation and Conjugate Addition of N-Boc-2-lithiopyrrolidine and N-Boc-2-lithiopiperidine.. ChemInform, 41(42).
- Synthesis of the core ring system of the stemona alkaloids by cascade condensation, cyclization, intramolecular cycloaddition.. Org Biomol Chem, 8(20), 4530-4532.
- ChemInform Abstract: Ring Expansion of Aziridines to Piperidines Using the Aza‐Wittig Rearrangement.. ChemInform, 26(36), no-no.
- Synthesis of Natural Products Using Intramolecular Dipolar Cycloaddition Reactions. CURR ORG SYNTH, 7(4), 312-331.
- Dynamic thermodynamic resolution of lithiated N-Boc-N '-alkylpiperazines. TETRAHEDRON LETT, 51(28), 3642-3644.
- Regioselective and stereoselective copper(I)-promoted allylation and conjugate addition of N-Boc-2-lithiopyrrolidine and N-Boc-2-lithiopiperidine.. J Org Chem, 75(12), 4069-4077.
- Asymmetric deprotonation of N-boc piperidine: react IR monitoring and mechanistic aspects.. J Am Chem Soc, 132(21), 7260-7261.
- Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement. TETRAHEDRON LETT, 51(18), 2457-2460. View this article in WRRO
- Asymmetric substitutions of 2-lithiated N-boc-piperidine and N-Boc-azepine by dynamic resolution.. Chemistry, 16(13), 4082-4090.
- ChemInform Abstract: Direct Preparation of 7-Allyl- and 7-Arylindolines.. ChemInform, 41(10).
- Dynamic resolutions of chiral organolithiums. Topics in Stereochemistry, 26, 253-293.
- Erratum: The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA (Chemical Communications (2009) (5239-5241) DOI: 10.1039/b911024k). Chemical Communications, 46(48), 9267-9268.
- Asymmetric substitutions of 2-lithiated N-boc-piperidine and N-Boc-azepine by dynamic resolution.. Chemistry (Weinheim an der Bergstrasse, Germany), 16(13), 4082-4090.
- Direct Preparation of 7-Allyl- and 7-Arylindolines. ADV SYNTH CATAL, 351(16), 2619-2623.
- The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA.. Chem Commun (Camb)(35), 5239-5241.
- ChemInform Abstract: Cascade Condensation, Cyclization, Intermolecular Dipolar Cycloaddition by Multi-Component Coupling and Application to a Synthesis of (.+-.)-Crispine A.. ChemInform, 40(35).
- ChemInform Abstract: Synthesis of Fused Tricyclic Amines from Enolizable Acyclic Aldehydes by Cyclization then Dipolar Cycloaddition Cascade: Synthesis of Myrioxazine A.. ChemInform, 40(33).
- ChemInform Abstract: Stereoselective Formation of Fused Tricyclic Amines from Acyclic Aldehydes by a Cascade Process Involving Condensation, Cyclization, and Dipolar Cycloaddition.. ChemInform, 40(30).
- Enantiomerization dynamics and a catalytic dynamic resolution of N-trimethylallyl-2-lithiopyrrolidine.. J Am Chem Soc, 131(20), 6908-6909.
- Cascade condensation, cyclization, intermolecular dipolar cycloaddition by multi-component coupling and application to a synthesis of (+/-)-crispine A.. Org Biomol Chem, 7(8), 1674-1679.
- Synthesis of fused tricyclic amines from enolizable acyclic aldehydes by cyclization then dipolar cycloaddition cascade: synthesis of myrioxazine A.. Org Lett, 11(7), 1515-1518.
- Stereoselective formation of fused tricyclic amines from acyclic aldehydes by a cascade process involving condensation, cyclization, and dipolar cycloaddition.. J Org Chem, 74(6), 2290-2300.
- ChemInform Abstract: Dynamic Resolution of N-Boc-2-lithiopiperidine.. ChemInform, 40(4).
- ChemInform Abstract: Synthesis of 2-Arylpiperidines by Palladium Couplings of Aryl Bromides with Organozinc Species Derived from Deprotonation of N-Boc-Piperidine.. ChemInform, 40(2).
- ChemInform Abstract: Cascade Cyclization Intermolecular Dipolar Cycloaddition by Multi-Component Couplings - Synthesis of Indolizidines and Pyrrolizidines.. ChemInform, 39(52).
- Dynamic resolution of N-Boc-2-lithiopiperidine.. Chem Commun (Camb)(35), 4174-4176.
- Cascade cyclization intermolecular dipolar cycloaddition by multi-component couplings - synthesis of indolizidines and pyrrolizidines. TETRAHEDRON LETT, 49(37), 5408-5410.
- Synthesis of 2-arylpiperidines by palladium couplings of aryl bromides with organozinc species derived from deprotonation of N-boc-piperidine.. Org Lett, 10(17), 3923-3925.
- ChemInform Abstract: Synthesis of Carboxylic Amides by Ring-Opening of Oxazolidinones with Grignard Reagents.. ChemInform, 39(34).
- ChemInform Abstract: Asymmetric Lithiation-Substitution of Amines Involving Rearrangement of Borates.. ChemInform, 39(23).
- Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents.. Org Biomol Chem, 6(8), 1410-1415.
- ChemInform Abstract: Dynamic Kinetic and Kinetic Resolution of N-Boc-2-lithiopiperidine.. ChemInform, 39(11).
- The barrier to enantiomerization of N-Boc-2-lithiopyrrolidine: the effect of chiral and achiral diamines.. Chem Commun (Camb)(1), 97-98.
- Asymmetric lithiation-substitution of amines involving rearrangement of borates.. Org Lett, 10(1), 141-143.
- Dynamic kinetic and kinetic resolution of N-Boc-2-lithiopiperidine.. Chem Commun (Camb)(43), 4534-4536.
- Asymmetric deprotonation of N-boc-piperidines. TETRAHEDRON-ASYMMETR, 18(17), 2113-2119.
- Highly Efficient Synthesis of Tricyclic Amines by a Cyclization/Cycloaddition Cascade: Total Syntheses of Aspidospermine, Aspidospermidine, and Quebrachamine. Angewandte Chemie, 119(32), 6271-6274.
- Intramolecular dipolar cycloaddition reactions to give substituted indoles - A formal synthesis of deethylibophyllidine. EUR J ORG CHEM(16), 2676-2686.
- Synthesis of tetracyclic indole-containing ring systems by intramolecular cycloadditions of azomethine ylides. TETRAHEDRON LETT, 48(5), 873-875.
- Highly efficient synthesis of tricyclic amines by a cyclization/cycloaddition cascade: total syntheses of aspidospermine, aspidospermidine, and quebrachamine.. Angew Chem Int Ed Engl, 46(32), 6159-6162.
- Asymmetric synthesis of 3-hydroxy-pyrrolidines via tin-lithium exchange and cyclization.. Org Lett, 8(20), 4469-4471.
- Dynamic thermodynamic and dynamic kinetic resolution of 2-lithiopyrrolidines.. J Am Chem Soc, 128(33), 10943-10951.
- Dynamic Kinetic Resolution of N-Boc-2-lithiopyrrolidine.. ChemInform, 36(43).
- Dipolar cycloaddition and ring-closing metathesis in the synthesis of the tetracyclic ABCE ring system of manzamine A. SYNLETT(11), 1743-1745.
- Intramolecular dipolar cycloaddition reactions of azomethine ylides.. Chem Rev, 105(7), 2765-2810.
- Dynamic kinetic resolution of N-Boc-2-lithiopyrrolidine.. Chem Commun (Camb)(24), 3083-3085.
- Dynamic resolution of N-alkyl-2-lithiopyrrolidines with the chiral ligand (-)-sparteine. TETRAHEDRON, 61(13), 3205-3220.
- Structural studies of {Li-6} 2-lithiopyrrolidines using NMR spectroscopy. TETRAHEDRON, 61(13), 3271-3280.
- Barrier to enantiomerization of unstabilized, chelated, and dipole-stabilized 2-lithiopyrrolidines.. J Am Chem Soc, 127(1), 449-457.
- Synthesis and biological studies of 1-amino beta-carbolines.. Bioorg Med Chem Lett, 14(23), 5841-5844.
- Intramolecular carbolithiation reactions for the preparation of 3-alkenylpyrrolidines.. Org Biomol Chem, 1(12), 2111-2119.
- Preparation of diamines by lithiation-substitution of imidazolidines and pyrimidines.. Org Biomol Chem, 1(9), 1532-1544.
- Enantioselective synthesis of substituted pyrrolidines by dynamic resolution.. Angew Chem Int Ed Engl, 41(20), 3887-3889.
- Synthesis of the ABC ring system of manzamine A.. J Org Chem, 67(17), 6181-6187.
- Intramolecular carbolithiation reactions of chiral alpha-amino-organolithium species.. Chemistry, 8(1), 195-207.
- Intramolecular carbolithiation reactions of chiral alpha-amino-organolithium species.. Chemistry (Weinheim an der Bergstrasse, Germany), 8(1).
- Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution.. Org Lett, 3(23), 3799-3801.
- Stereoselective synthesis of pyrrolidines and pyrrolizidines by intramolecular carbolithiation. SYNTHESIS-STUTTGART(10), 1523-1531.
- Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles. J CHEM SOC PERK T 1(15), 1758-1763.
- ChemInform Abstract: Intramolecular Carbolithiation Reactions for the Preparation of Azabicyclo[2.2.1]heptanes.. ChemInform, 31(43), no-no.
- ChemInform Abstract: Chiral Organolithium Species: Determination of the Rate of Cyclization and Extent of Racemization.. ChemInform, 31(49), no-no.
- Intramolecular carbolithiation reactions for the preparation of Azabicyclo. J Org Chem, 65(12), 3788-3795.
- A convenient route to N-alkyl-2-tributylstannyl-pyrrolidines involving reductive amination. TETRAHEDRON LETT, 41(13), 2235-2237.
- A rapid approach to amino-acid derivatives by [2,3]-Stevens rearrangement. SYNLETT(2), 236-238.
- Chiral organolithium species: determination of the rate of cyclization and extent of racemization. CHEM COMMUN(17), 1569-1570.
- A new stereoselective approach to the manzamine alkaloids. CHEM COMMUN(17), 1757-1758.
- Meisenheimer rearrangements of N-allyl 2-azabornane derivatives. J CHEM SOC PERK T 1(16), 2327-2334.
- Synthesis of 7-azabicyclo[2.2.1]heptanes by anionic cyclization. TETRAHEDRON LETT, 40(9), 1819-1822.
- Proton abstraction and electrophilic quench at C-2 of imidazolidines. TETRAHEDRON, 54(47), 14255-14264.
- N,N '-bisacylimidazolidines from 1,2-diamines. SYNTHESIS-STUTTGART(10), 1463-1466.
- Investigations into the [2,3]-aza-Wittig rearrangement of N-alkyl N-allyl alpha-amino esters. J CHEM SOC PERK T 1(17), 2817-2821.
- Studies into the asymmetric Meisenheimer rearrangement. TETRAHEDRON-ASYMMETR, 9(11), 1995-2009.
- Main group organometallics in synthesis. J CHEM SOC PERK T 1(7), 1343-1364.
- Stereoselective anionic cyclizations to pyrrolidines. TETRAHEDRON LETT, 38(43), 7617-7620.
- Synthesis of pyrrolidines by anionic cyclization onto allylic ethers, alkynes and carboxylic groups. TETRAHEDRON LETT, 38(43), 7621-7624.
- N-alkylation and [2,3]-sigmatropic rearrangement of N-allyl alpha-amino esters. J CHEM SOC PERK T 1(20), 2951-2952.
- Preparation of beta-amino alcohols by carbon-carbon bond formation using substituted lithiomethylpyrrolidines. J CHEM SOC PERK T 1(10), 1481-1485.
- Main group organometallics in synthesis. CONTEMP ORG SYNTH, 4(2), 136-163.
- Chirality transfer from nitrogen to carbon in the [2,3]-Meisenheimer rearrangement. SYNLETT(3), 322-&.
- One-pot synthesis of N,N'-bisacylimidazolidines; Potential new acyl anion equivalents. SYNLETT(11), 1109-&.
- Synthesis of 3-alkylpyrrolidines by anionic cyclization. TETRAHEDRON, 52(38), 12541-12552.
- Anionic cyclizations of alpha-aminoorganolithiums. Determination of the stereoselectivity at the carbanion center and the synthesis of (+)-pseudoheliotridane. J AM CHEM SOC, 118(22), 5322-5323.
- SYNTHESIS OF 4-PHENYLPIPERIDINES BY TANDEM WITTIG OLEFINATION-AZA-WITTIG REARRANGEMENT OF 2-BENZOYLAZIRIDINES. J CHEM SOC PERK T 1(21), 2739-2745.
- NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - ALPHA-N-TOSYLAMINATION OF TRIISOPROPYLSILYL ENOL ETHERS. TETRAHEDRON, 51(41), 11087-11110.
- PYRROLIDINES BY 1,3-DIPOLAR CYCLOADDITION OF CONJUGATED AZOMETHINE YLIDES. SYNTHESIS-STUTTGART(9), 1147-&.
- RING EXPANSION OF AZIRIDINES TO PIPERIDINES USING THE AZA-WITTIG REARRANGEMENT. TETRAHEDRON LETT, 36(20), 3557-3560.
- A NEW ROUTE TO CYCLIC AMINES BY ANIONIC CYCLIZATION. TETRAHEDRON LETT, 36(12), 2157-2160.
- SYNTHESIS OF CYCLIC AMINES AND ALLYLIC SULFIDES BY PHENYLTHIO MIGRATION OF BETA-HYDROXY SULFIDES. J CHEM SOC PERK T 1(14), 1637-1656.
- AZA-WITTIG REARRANGEMENTS AND CYCLIZATIONS BY TRANSMETALATION OF N-BENZYLAMINOMETHYLSTANNANES. J CHEM SOC PERK T 1(12), 1275-1276.
- STEREOSPECIFIC PHENYLTHIO MIGRATIONS IN THE SYNTHESIS OF SPIROCYCLIC LACTONES AND ETHERS FROM N-METHYL-4-PIPERIDONE AND QUINUCLIDIN-3-ONE. J CHEM SOC PERK T 1(18), 2303-2307.
- TRANSFORMATION OF CYCLIC ALPHA-PHENYLTHIO ALDEHYDES BY STEREOSELECTIVE ALDOL REACTIONS AND PHENYLTHIO MIGRATION INTO SPIROCYCLIC LACTONES AND ETHERS, AND E-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS. J CHEM SOC PERK T 1(2), 451-460.
- NEW TRIALKYLSILYL ENOL ETHER CHEMISTRY - SYNTHESIS OF THE BENZOMORPHANONE CORE STRUCTURE USING A STEREOELECTRONIC CONFORMATIONAL LOCK. J AM CHEM SOC, 113(2), 672-673.
- STEREOCONTROLLED AMIDOCYCLIZATIONS WITH PHENYLTHIO MIGRATION. TETRAHEDRON LETT, 30(43), 5937-5940.
- STEREOCHEMICALLY CONTROLLED SYNTHESIS OF SPIROCYCLIC LACTONES AND ETHERS FROM N-METHYL-4-PIPERIDONE AND 3-QUINUCLIDINONE BY PHENYLTHIO MIGRATION. TETRAHEDRON LETT, 29(41), 5321-5324.
- STEREOCHEMICAL CONTROL IN THE SYNTHESIS OF TETRAHYDROFURANS BY CYCLIZATION OF DIOLS WITH PHENYLTHIO MIGRATION. TETRAHEDRON LETT, 29(38), 4885-4888.
- Synthesis of Enantioenriched Spirocyclic 2-Arylpiperidines via Kinetic Resolution. Organic & Biomolecular Chemistry.
- Regiochemical and Stereochemical Studies of the Intramolecular Dipolar Cycloaddition of Nitrones Derived from Quaternary Aldehydes. Synlett, 27(03), 447-449. View this article in WRRO
- Synthesis of the tricyclic core of manzamine A. Organic & Biomolecular Chemistry, 13(11), 3331-3340. View this article in WRRO
- ChemInform Abstract: Synthesis of 3-Alkylpyrrolidines by Anionic Cyclization.. ChemInform, 28(3), no-no.
- ChemInform Abstract: Synthesis of 2-Hydroxy-3-indolinones and 3-Hydroxy-2-indolinones by Anionic Cyclization, in situ Oxidation and Rearrangement.. ChemInform, 41(34), no-no.
- ChemInform Abstract: Transformation of Cyclic α-Phenylthio Aldehydes by Stereoselective Aldol Reactions and Phenylthio Migration into Spirocyclic Lactones and Ethers, and E-Allylic Alcohols with 1,4- Related Chiral Centers.. ChemInform, 22(18), no-no.
- ChemInform Abstract: New Trialkylsilyl Enol Ether Chemistry. Synthesis of the Benzomorphanone Core Structure Using a Stereoelectronic Conformational Lock.. ChemInform, 22(21), no-no.
- ChemInform Abstract: Stereospecific Phenylthio Migrations in the Synthesis of Spirocyclic Lactones and Ethers from N-Methyl-4-piperidone and Quinuclidin-3-one.. ChemInform, 24(1), no-no.
- ChemInform Abstract: Synthesis of Cyclic Amines and Allylic Sulfides by Phenylthio Migration of β-Hydroxy Sulfides.. ChemInform, 24(47), no-no.
- ChemInform Abstract: Aza-Wittig Rearrangements and Cyclizations by Transmetalation of N- Benzylaminomethylstannanes.. ChemInform, 24(42), no-no.
- ChemInform Abstract: A New Route to Cyclic Amines by Anionic Cyclization.. ChemInform, 26(30), no-no.
- ChemInform Abstract: New Trialkylsilyl Enol Ether Chemistry: α-N-Tosylamination of Triisopropylsilyl Enol Ethers.. ChemInform, 27(5), no-no.
- ChemInform Abstract: Synthesis of 4-Phenylpiperidines by Tandem Wittig Olefination-Aza- Wittig Rearrangement of 2-Benzoylaziridines.. ChemInform, 27(9), no-no.
- ChemInform Abstract: Pyrrolidines by 1,3-Dipolar Cycloaddition of Conjugated Azomethine Ylides.. ChemInform, 27(2), no-no.
- ChemInform Abstract: One or More CH and/or CC Bond(s) Formed by Rearrangement. ChemInform, 27(31), no-no.
- ChemInform Abstract: Anionic Cyclizations of α-Aminoorganolithiums. Determination of the Stereoselectivity at the Carbanion Center and the Synthesis of (+)- Pseudoheliotridane.. ChemInform, 27(38), no-no.
- ChemInform Abstract: One-Pot Synthesis of N,N′-Bisacylimidazolidines; Potential New Acyl Anion Equivalents.. ChemInform, 28(15), no-no.
- ChemInform Abstract: Preparation of β-Amino Alcohols by Carbon-Carbon Bond Formation Using Substituted Lithiomethylpyrrolidines.. ChemInform, 28(42), no-no.
- ChemInform Abstract: Main Group Organometallics in Synthesis. ChemInform, 28(31), no-no.
- ChemInform Abstract: Chirality Transfer from Nitrogen to Carbon in the (2,3)-Meisenheimer Rearrangement.. ChemInform, 28(40), no-no.
- ChemInform Abstract: Synthesis of Pyrrolidines by Anionic Cyclization onto Allylic Ethers, Alkynes, and Carboxylic Groups.. ChemInform, 29(5), no-no.
- ChemInform Abstract: Stereoselective Anionic Cyclizations to Pyrrolidines.. ChemInform, 29(5), no-no.
- ChemInform Abstract: N-Alkylation and [2,3]-Sigmatropic Rearrangement of N-Allyl α-Amino Esters.. ChemInform, 29(6), no-no.
- ChemInform Abstract: Main Group Organometallics in Synthesis. ChemInform, 29(35), no-no.
- ChemInform Abstract: Studies into the Asymmetric Meisenheimer Rearrangement.. ChemInform, 29(42), no-no.
- ChemInform Abstract: N,N′-Bisacylimidazolidines from 1,2-Diamines.. ChemInform, 30(4), no-no.
- ChemInform Abstract: Proton Abstraction and Electrophilic Quench at C-2 of Imidazolidines.. ChemInform, 30(10), no-no.
- ChemInform Abstract: Synthesis of 7-Azabicyclo[2.2.1]heptanes by Anionic Cyclization.. ChemInform, 30(22), no-no.
- ChemInform Abstract: A New Stereoselective Approach to the Manzamine Alkaloids.. ChemInform, 30(44), no-no.
- ChemInform Abstract: Meisenheimer Rearrangements of N-Allyl 2-Azabornane Derivatives.. ChemInform, 30(50), no-no.
- ChemInform Abstract: A Rapid Approach to Amino-Acid Derivatives by [2,3]-Stevens Rearrangement.. ChemInform, 31(21), no-no.
- ChemInform Abstract: A Convenient Route to N-Alkyl-2-tributylstannyl-pyrrolidines Involving Reductive Amination.. ChemInform, 31(25), no-no.
- ChemInform Abstract: Intramolecular Azomethine Ylide Cycloaddition Reactions to Give Octahydroindoles.. ChemInform, 32(52), no-no.
- ChemInform Abstract: Stereoselective Synthesis of Pyrrolidines and Pyrrolizidines by Intramolecular Carbolithiation.. ChemInform, 32(45), no-no.
- ChemInform Abstract: Synthesis of Chiral 1,2-Diamines by Asymmetric Lithiation-Substitution.. ChemInform, 33(13), no-no.
- ChemInform Abstract: Intramolecular Carbolithiation Reactions of Chiral α-Amino-organolithium Species.. ChemInform, 33(23), no-no.
Chapters
- 2.1.2 Domino Reactions Including [2 + 2], [3 + 2], or [5 + 2] Cycloadditions In Snyder SA & Schaumann E (Ed.), Applications of Domino Transformations in Organic Synthesis 2 Georg Thieme Verlag
- α-Amino-Organolithium Compounds John Wiley & Sons, Ltd
Conference proceedings papers
- ORGN 422-Highly efficient synthesis of tricyclic amines by a cyclization/cycloaddition cascade: Total syntheses of aspidospermidine, aspidospermine and quebrachamine. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, Vol. 235
- Towards the total synthesis of manzamine a using 1,3 dipolar cycloaddition of azomethine ylides.. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, Vol. 229 (pp U370-U370)
- Enantiomerization of unstabilized and dipole-stabilized 2-lithiopyrrolidines: (Absolute) barrier to inversion. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, Vol. 226 (pp U149-U149)
- Dynamic resolution of alpha-amino-organolithium species.. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, Vol. 226 (pp U169-U169)
- Synthesis of the core ring system of manzamine A using azomethine ylide cycloaddition chemistry.. ABSTR PAP AM CHEM S, Vol. 221 (pp U100-U100)
- Applications of Domino Transformations in Organic Synthesis 2. Georg Thieme Verlag KG.
- Teaching interests
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Organic Chemistry
- Teaching activities
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Undergraduate and postgraduate taught modules
- Organic Reaction Mechanisms (Level 2)
This segment introduces substitution and elimination reactions. - Frontier Molecular Orbital Theory (Levels 3 & 4)
This segment introduces the applications of frontier molecular orbital theory in organic chemistry to understand conformation and reactivity. - Organic Chemistry of the Main Group Elements (Level 4)
This segment surveys the synthetic and mechanistic features of a range of organoelement reagents in the context of modern organic synthesis.
Support Teaching:
- Tutorials: Level 1 General Chemistry
- Level 3 Literature Review
Laboratory Teaching:
- Level 3 Organic Laboratories
- Level 4 Research Project
- Organic Reaction Mechanisms (Level 2)