Research support from the Skaggs Institute for Chemical Biology is gratefully acknowledged. We also thank Dr. A. L. Rheingold and Dr. C. E. Moore for the X-ray crystallographic analysis. G.H.-T. also thanks Universidad Autónoma de Madrid for financial support.
Rationally Designed Amide Donors for Organocatalytic Asymmetric Michael Reactions†
Article first published online: 13 APR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 22, pages 5381–5385, May 29, 2012
How to Cite
Tan, B., Hernández-Torres, G. and Barbas, C. F. (2012), Rationally Designed Amide Donors for Organocatalytic Asymmetric Michael Reactions . Angew. Chem. Int. Ed., 51: 5381–5385. doi: 10.1002/anie.201200996
- Issue published online: 23 MAY 2012
- Article first published online: 13 APR 2012
- Manuscript Received: 6 FEB 2012
- Skaggs Institute for Chemical Biology
- asymmetric synthesis;
- cinchona alkaloids;
- Michael addition;
Amide nucleophiles on demand: Rationally designed pyrazoleamides function as Michael donors in urea-catalyzed asymmetric Michael reactions with excellent chemical and optical yields (see scheme). The pyrazoleamide group performs as an ester equivalent, a directing group, an activating group, and functions as a good leaving group in further transformations of the product.