Research support was generously provided by the NIH/NIGMS (RO1 GM73072), Abbott Laboratories, Amgen, 3M, and Boerhinger-Ingelheim. A.C. is the recipient of a Dow Chemical Company Fellowship. We thank T. Reynolds and C. Stern (NU) for assistance with X-ray crystallography. Funding for the NU Analytical Services Laboratory has been furnished in part by the NSF (CHE-9871268).
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Communication
A Highly Enantioselective Intramolecular Michael Reaction Catalyzed by N-Heterocyclic Carbenes†
Article first published online: 15 MAR 2007
DOI: 10.1002/anie.200605235
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Phillips, E., Wadamoto, M., Chan, A. and Scheidt, K. (2007), A Highly Enantioselective Intramolecular Michael Reaction Catalyzed by N-Heterocyclic Carbenes. Angewandte Chemie International Edition, 46: 3107–3110. doi: 10.1002/anie.200605235
- †
Publication History
- Issue published online: 12 APR 2007
- Article first published online: 15 MAR 2007
- Manuscript Revised: 2 FEB 2007
- Manuscript Received: 27 DEC 2006
Funded by
- NIH/NIGMS. Grant Number: RO1 GM73072
- Abbott Laboratories
- Amgen
- 3M
- Boerhinger-Ingelheim
- NSF. Grant Number: CHE-9871268
Keywords:
- acylation;
- asymmetric catalysis;
- Michael addition;
- N-heterocyclic carbenes;
- synthetic methods
Graphical Abstract
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).