Highly Enantioselective Conjugate Additions to α,β-Unsaturated Ketones Catalyzed by a (Salen)Al Complex

Mark S. Taylor, David N. Zalatan, Andreas M. Lerchner, and Eric N. Jacobsen*
Contribution from the Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138
J. Am. Chem. Soc., 2005, 127 (4), pp 1313–1317
DOI: 10.1021/ja044999s
Publication Date (Web): January 6, 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.

, jacobsen@chemistry.harvard.edu

Abstract

Abstract Image

Chiral (salen)Al complex 1a catalyzes the highly enantioselective conjugate addition of carbon- and nitrogen-based nucleophiles to acyclic α,β-unsaturated ketones. This methodology is tolerant of substantial variation of the ketone structure, providing access to a wide range of useful chiral building blocks in high yield and enantiomeric excess. Synthetic manipulations of the conjugate addition products are demonstrated, including the straightforward preparation of β-amino ketones and highly enantioenriched carbo- and heterocyclic compounds.

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History

  • Published In Issue February 02, 2005
  • Received August 18, 2004

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