A Highly Enantio- and Diastereoselective Catalytic Intramolecular Stetter Reaction

Javier Read de Alaniz and Tomislav Rovis*
Contribution from the Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523
J. Am. Chem. Soc., 2005, 127 (17), pp 6284–6289
DOI: 10.1021/ja0425132
Publication Date (Web): April 2, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rovis@lamar.colostate.edu

Abstract

Abstract Image

A highly enantio- and diastereoselective intramolecular Stetter reaction has been developed. Subjection of α,α-disubstituted Michael acceptors to an asymmetric intramolecular Stetter reaction results in a highly enantioselective conjugate addition and a diastereoselective proton transfer. Available evidence suggests the diastereoselective protonation occurs via intramolecular delivery to the sterically more hindered face of the enolate. The scope of the trisubstituted Michael acceptors has been examined and found to be broad with respect to the size of the α-substituent and nature of the Michael acceptor. Aliphatic and aromatic aldehydes were examined and found to afford the desired product in good overall yield with high enantio- and diastereoselectivity.

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History

  • Published In Issue May 04, 2005
  • Received December 13, 2004

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