M.M. is a Dale F. and Betty Ann Frey Damon Runyon Scholar supported by the Damon Runyon Cancer Research Foundation (DRS-39-04). M.M. is a Firmenich Assistant Professor of Chemistry. We acknowledge financial support by NIH-NIGMS (GM074825), Amgen Inc., and Boehringer Ingelheim Pharmaceutical Inc.
Stereoselective Intermolecular Formal [3+3] Cycloaddition Reaction of Cyclic Enamines and Enones†
Article first published online: 5 DEC 2006
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 46, Issue 4, pages 565–568, January 15, 2007
How to Cite
Movassaghi, M. and Chen, B. (2007), Stereoselective Intermolecular Formal [3+3] Cycloaddition Reaction of Cyclic Enamines and Enones. Angew. Chem. Int. Ed., 46: 565–568. doi: 10.1002/anie.200603302
- Issue published online: 10 JAN 2007
- Article first published online: 5 DEC 2006
- Manuscript Received: 11 AUG 2006
- Damon Runyon Cancer Research Foundation. Grant Number: DRS-39-04
- Amgen Inc.
- Boehringer Ingelheim Pharmaceutical Inc
- conjugate addition;
A convergent strategy for the synthesis of tricyclic imino alcohols was partly inspired by a postulated biosynthesis of galbulimima alkaloids. In this sequential α,α′ alkylation of unsymmetrical ketoimines, at least three stereocenters are created with a high level of diastereoselectivity. Organocatalytic and asymmetric variants of this methodology complement an organocuprate-based approach (see scheme).