Efficient N-Heterocyclic Carbene-Catalyzed O- to C-acyl Transfer

J E Thomson; K Rix; Andrew David Smith

doi:10.1021/ol061380h

Efficient N-Heterocyclic Carbene-Catalyzed O- to C-acyl Transfer

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

Abstract

An N-heterocyclic carbene promotes the rearrangement of alpha-amino acid derived O-acyl carbonates to their corresponding C-acylated isomers, generating a C-C bond and a quaternary stereocenter with high efficiency, under mild reaction conditions and with low catalyst loadings.

Original language	English
Pages (from-to)	3785-3788
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	17
DOIs	https://doi.org/10.1021/ol061380h
Publication status	Published - 17 Aug 2006

Keywords

INTRAMOLECULAR STETTER REACTION
NUCLEOPHILIC CARBENES
TRANSESTERIFICATION/ACYLATION REACTIONS
ALPHA,BETA-UNSATURATED ALDEHYDES
LIVING POLYMERIZATION
GAMMA-BUTYROLACTONES
QUATERNARY CARBON
1ST EXAMPLE
ACYLATION
ESTERS

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10.1021/ol061380h

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@article{87aa140af1634391a00072d2a8093045,

title = "Efficient N-Heterocyclic Carbene-Catalyzed O- to C-acyl Transfer",

abstract = "An N-heterocyclic carbene promotes the rearrangement of alpha-amino acid derived O-acyl carbonates to their corresponding C-acylated isomers, generating a C-C bond and a quaternary stereocenter with high efficiency, under mild reaction conditions and with low catalyst loadings.",

keywords = "INTRAMOLECULAR STETTER REACTION, NUCLEOPHILIC CARBENES, TRANSESTERIFICATION/ACYLATION REACTIONS, ALPHA,BETA-UNSATURATED ALDEHYDES, LIVING POLYMERIZATION, GAMMA-BUTYROLACTONES, QUATERNARY CARBON, 1ST EXAMPLE, ACYLATION, ESTERS",

author = "Thomson, {J E} and K Rix and Smith, {Andrew David}",

note = "First fully independent paper as PI since move to St Andrews in the internationally competitive area of organocatalysis",

year = "2006",

month = aug,

day = "17",

doi = "10.1021/ol061380h",

language = "English",

volume = "8",

pages = "3785--3788",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "17",

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TY - JOUR

T1 - Efficient N-Heterocyclic Carbene-Catalyzed O- to C-acyl Transfer

AU - Thomson, J E

AU - Rix, K

AU - Smith, Andrew David

N1 - First fully independent paper as PI since move to St Andrews in the internationally competitive area of organocatalysis

PY - 2006/8/17

Y1 - 2006/8/17

N2 - An N-heterocyclic carbene promotes the rearrangement of alpha-amino acid derived O-acyl carbonates to their corresponding C-acylated isomers, generating a C-C bond and a quaternary stereocenter with high efficiency, under mild reaction conditions and with low catalyst loadings.

AB - An N-heterocyclic carbene promotes the rearrangement of alpha-amino acid derived O-acyl carbonates to their corresponding C-acylated isomers, generating a C-C bond and a quaternary stereocenter with high efficiency, under mild reaction conditions and with low catalyst loadings.

KW - INTRAMOLECULAR STETTER REACTION

KW - NUCLEOPHILIC CARBENES

KW - TRANSESTERIFICATION/ACYLATION REACTIONS

KW - ALPHA,BETA-UNSATURATED ALDEHYDES

KW - LIVING POLYMERIZATION

KW - GAMMA-BUTYROLACTONES

KW - QUATERNARY CARBON

KW - 1ST EXAMPLE

KW - ACYLATION

KW - ESTERS

UR - http://www.scopus.com/inward/record.url?scp=33748629399&partnerID=8YFLogxK

UR - http://pubs.acs.org/cgi-bin/article.cgi/orlef7/2006/8/i17/pdf/ol061380h.pdf

U2 - 10.1021/ol061380h

DO - 10.1021/ol061380h

M3 - Article

SN - 1523-7060

VL - 8

SP - 3785

EP - 3788

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Efficient N-Heterocyclic Carbene-Catalyzed O- to C-acyl Transfer

Abstract

Keywords

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