N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates

Jennifer E. Thomson; Andrew F. Kyle; Katherine A. Gallagher; Philip Lenden; Carmen Concellon; Louis C. Morrill; Andrew J. Miller; Caroline Joannesse; Alexandra M. Z. Slawin; Andrew D. Smith

doi:10.1055/s-2008-1077890

N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates

Jennifer E. Thomson, Andrew F. Kyle, Katherine A. Gallagher, Philip Lenden, Carmen Concellon, Louis C. Morrill, Andrew J. Miller, Caroline Joannesse, Alexandra M. Z. Slawin, Andrew D. Smith

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

Abstract

The ability of N-heterocyclic carbenes to promote O-to-C carboxyl transfer on a range of indolyl and benzofuranyl carbonates is examined, and the scope and limitations of this process delineated.

Original language	English
Pages (from-to)	2805-2818
Number of pages	14
Journal	Synthesis
DOIs	https://doi.org/10.1055/s-2008-1077890
Publication status	Published - 2 Sept 2008

Keywords

N-heterocyclic carbene
catalysis
carboxyl transfer
ENANTIOSELECTIVE TOTAL-SYNTHESIS
INTRAMOLECULAR STETTER REACTION
DIELS-ALDER REACTIONS
ASYMMETRIC-SYNTHESIS
QUATERNARY CARBON
ALPHA,BETA-UNSATURATED ALDEHYDES
STEREOSELECTIVE-SYNTHESIS
NUCLEOPHILIC CARBENES
GAMMA-BUTYROLACTONES
EFFICIENT CATALYST

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@article{174d5293b5414ffcb0f8419a60e902cf,

title = "N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates",

abstract = "The ability of N-heterocyclic carbenes to promote O-to-C carboxyl transfer on a range of indolyl and benzofuranyl carbonates is examined, and the scope and limitations of this process delineated.",

keywords = "N-heterocyclic carbene, catalysis, carboxyl transfer, ENANTIOSELECTIVE TOTAL-SYNTHESIS, INTRAMOLECULAR STETTER REACTION, DIELS-ALDER REACTIONS, ASYMMETRIC-SYNTHESIS, QUATERNARY CARBON, ALPHA,BETA-UNSATURATED ALDEHYDES, STEREOSELECTIVE-SYNTHESIS, NUCLEOPHILIC CARBENES, GAMMA-BUTYROLACTONES, EFFICIENT CATALYST",

author = "Thomson, \{Jennifer E.\} and Kyle, \{Andrew F.\} and Gallagher, \{Katherine A.\} and Philip Lenden and Carmen Concellon and Morrill, \{Louis C.\} and Miller, \{Andrew J.\} and Caroline Joannesse and Slawin, \{Alexandra M. Z.\} and Smith, \{Andrew D.\}",

year = "2008",

month = sep,

day = "2",

doi = "10.1055/s-2008-1077890",

language = "English",

pages = "2805--2818",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

}

TY - JOUR

T1 - N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates

AU - Thomson, Jennifer E.

AU - Kyle, Andrew F.

AU - Gallagher, Katherine A.

AU - Lenden, Philip

AU - Concellon, Carmen

AU - Morrill, Louis C.

AU - Miller, Andrew J.

AU - Joannesse, Caroline

AU - Slawin, Alexandra M. Z.

AU - Smith, Andrew D.

PY - 2008/9/2

Y1 - 2008/9/2

N2 - The ability of N-heterocyclic carbenes to promote O-to-C carboxyl transfer on a range of indolyl and benzofuranyl carbonates is examined, and the scope and limitations of this process delineated.

AB - The ability of N-heterocyclic carbenes to promote O-to-C carboxyl transfer on a range of indolyl and benzofuranyl carbonates is examined, and the scope and limitations of this process delineated.

KW - N-heterocyclic carbene

KW - catalysis

KW - carboxyl transfer

KW - ENANTIOSELECTIVE TOTAL-SYNTHESIS

KW - INTRAMOLECULAR STETTER REACTION

KW - DIELS-ALDER REACTIONS

KW - ASYMMETRIC-SYNTHESIS

KW - QUATERNARY CARBON

KW - ALPHA,BETA-UNSATURATED ALDEHYDES

KW - STEREOSELECTIVE-SYNTHESIS

KW - NUCLEOPHILIC CARBENES

KW - GAMMA-BUTYROLACTONES

KW - EFFICIENT CATALYST

UR - https://www.scopus.com/pages/publications/51949090002

U2 - 10.1055/s-2008-1077890

DO - 10.1055/s-2008-1077890

M3 - Article

SN - 0039-7881

SP - 2805

EP - 2818

JO - Synthesis

JF - Synthesis

ER -

N-heterocyclic carbene catalysed oxygen-to-carbon carboxyl transfer of indolyl and benzofuranyl carbonates

Abstract

Keywords

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