N-Heterocyclic carbene catalysed β-lactam synthesis

Nicolas Fabien Denis Duguet; Craig Donald Campbell; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1039/b800857b

N-Heterocyclic carbene catalysed β-lactam synthesis

Nicolas Fabien Denis Duguet, Craig Donald Campbell, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journal › Article › peer-review

Abstract

N-Heterocyclic carbenes promote the formal [2+2] cycloaddition of ketenes with N-tosyl imines to give the corresponding beta-lactams in good to excellent isolated yields; chiral NHCs give beta-lactams in high e. e. after crystallisation.

Original language	English
Pages (from-to)	1108-1113
Number of pages	6
Journal	Organic & Biomolecular Chemistry
Volume	6
Issue number	6
Early online date	12 Feb 2008
DOIs	https://doi.org/10.1039/b800857b
Publication status	Published - 2008

Keywords

DIELS-ALDER REACTIONS
ASYMMETRIC-SYNTHESIS
STAUDINGER REACTION
DIRECT ANNULATIONS
AMINO-ACIDS
ALPHA,BETA-UNSATURATED ALDEHYDES
ENANTIOSELECTIVE SYNTHESIS
GAMMA-BUTYROLACTONES
ENALS
IMINES

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@article{362a3af48fc14720b8d573abb2e3de57,

title = "N-Heterocyclic carbene catalysed β-lactam synthesis",

abstract = "N-Heterocyclic carbenes promote the formal [2+2] cycloaddition of ketenes with N-tosyl imines to give the corresponding beta-lactams in good to excellent isolated yields; chiral NHCs give beta-lactams in high e. e. after crystallisation.",

keywords = "DIELS-ALDER REACTIONS, ASYMMETRIC-SYNTHESIS, STAUDINGER REACTION, DIRECT ANNULATIONS, AMINO-ACIDS, ALPHA,BETA-UNSATURATED ALDEHYDES, ENANTIOSELECTIVE SYNTHESIS, GAMMA-BUTYROLACTONES, ENALS, IMINES",

author = "Duguet, {Nicolas Fabien Denis} and Campbell, {Craig Donald} and Slawin, {Alexandra Martha Zoya} and Smith, {Andrew David}",

year = "2008",

doi = "10.1039/b800857b",

language = "English",

volume = "6",

pages = "1108--1113",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "6",

}

TY - JOUR

T1 - N-Heterocyclic carbene catalysed β-lactam synthesis

AU - Duguet, Nicolas Fabien Denis

AU - Campbell, Craig Donald

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

PY - 2008

Y1 - 2008

N2 - N-Heterocyclic carbenes promote the formal [2+2] cycloaddition of ketenes with N-tosyl imines to give the corresponding beta-lactams in good to excellent isolated yields; chiral NHCs give beta-lactams in high e. e. after crystallisation.

AB - N-Heterocyclic carbenes promote the formal [2+2] cycloaddition of ketenes with N-tosyl imines to give the corresponding beta-lactams in good to excellent isolated yields; chiral NHCs give beta-lactams in high e. e. after crystallisation.

KW - DIELS-ALDER REACTIONS

KW - ASYMMETRIC-SYNTHESIS

KW - STAUDINGER REACTION

KW - DIRECT ANNULATIONS

KW - AMINO-ACIDS

KW - ALPHA,BETA-UNSATURATED ALDEHYDES

KW - ENANTIOSELECTIVE SYNTHESIS

KW - GAMMA-BUTYROLACTONES

KW - ENALS

KW - IMINES

U2 - 10.1039/b800857b

DO - 10.1039/b800857b

M3 - Article

SN - 1477-0520

VL - 6

SP - 1108

EP - 1113

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 6

ER -

N-Heterocyclic carbene catalysed β-lactam synthesis

Abstract

Keywords

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