A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes

Eric M. Phillips; Manabu Wadamoto; Audrey Chan; Karl A. Scheidt

doi:10.1002/anie.200605235

A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes

Eric M. Phillips^*, Manabu Wadamoto, Audrey Chan, Karl A. Scheidt

^*Corresponding author for this work

Chemistry

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

188 Scopus citations

Abstract

(Chemical Equation Presented) Metal-less Michael: A highly diastereo-and enantioselective intramolecular Michael addition of α,β-unsaturated aldehydes to enones catalyzed by an N-heterocyclic carbene (NHC) has been developed. The reaction is tolerant of alkyl and aromatic substituents, as well as saturated and unsaturated tethers between the enal and conjugate acceptor (see scheme).

Original language	English (US)
Pages (from-to)	3107-3110
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	17
DOIs	https://doi.org/10.1002/anie.200605235
State	Published - 2007

Keywords

Acylation
Asymmetric catalysis
Michael addition
N-heterocyclic carbenes
Synthetic methods

ASJC Scopus subject areas

General Chemistry
Catalysis

Access to Document

10.1002/anie.200605235

Cite this

@article{e8f7839d418e46a0aed8f1cf4dd7de64,

title = "A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes",

abstract = "(Chemical Equation Presented) Metal-less Michael: A highly diastereo-and enantioselective intramolecular Michael addition of α,β-unsaturated aldehydes to enones catalyzed by an N-heterocyclic carbene (NHC) has been developed. The reaction is tolerant of alkyl and aromatic substituents, as well as saturated and unsaturated tethers between the enal and conjugate acceptor (see scheme).",

keywords = "Acylation, Asymmetric catalysis, Michael addition, N-heterocyclic carbenes, Synthetic methods",

author = "Phillips, {Eric M.} and Manabu Wadamoto and Audrey Chan and Scheidt, {Karl A.}",

year = "2007",

doi = "10.1002/anie.200605235",

language = "English (US)",

volume = "46",

pages = "3107--3110",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "17",

}

TY - JOUR

T1 - A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes

AU - Phillips, Eric M.

AU - Wadamoto, Manabu

AU - Chan, Audrey

AU - Scheidt, Karl A.

PY - 2007

Y1 - 2007

N2 - (Chemical Equation Presented) Metal-less Michael: A highly diastereo-and enantioselective intramolecular Michael addition of α,β-unsaturated aldehydes to enones catalyzed by an N-heterocyclic carbene (NHC) has been developed. The reaction is tolerant of alkyl and aromatic substituents, as well as saturated and unsaturated tethers between the enal and conjugate acceptor (see scheme).

AB - (Chemical Equation Presented) Metal-less Michael: A highly diastereo-and enantioselective intramolecular Michael addition of α,β-unsaturated aldehydes to enones catalyzed by an N-heterocyclic carbene (NHC) has been developed. The reaction is tolerant of alkyl and aromatic substituents, as well as saturated and unsaturated tethers between the enal and conjugate acceptor (see scheme).

KW - Acylation

KW - Asymmetric catalysis

KW - Michael addition

KW - N-heterocyclic carbenes

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=34250822311&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34250822311&partnerID=8YFLogxK

U2 - 10.1002/anie.200605235

DO - 10.1002/anie.200605235

M3 - Article

C2 - 17366506

AN - SCOPUS:34250822311

SN - 1433-7851

VL - 46

SP - 3107

EP - 3110

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 17

ER -

A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 631931: Experimental Crystal Structure Determination

Cite this

A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 631931: Experimental Crystal Structure Determination

Cite this