Highly Enantioselective, Catalytic Conjugate Addition of Cyanide to α,β-Unsaturated Imides

Glenn M. Sammis and Eric N. Jacobsen*
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138
J. Am. Chem. Soc., 2003, 125 (15), pp 4442–4443
DOI: 10.1021/ja034635k
Publication Date (Web): March 25, 2003
Copyright © 2003 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

(Salen)Al−Cl complex 1a catalyzes the asymmetric conjugate addition of hydrogen cyanide to α,β-unsaturated imides in high yields and enantioselectivities. The cyanide adducts can readily be converted into a variety of useful chiral building blocks, including α-substituted-β-amino acids and β-substituted-γ-aminobutyric acids. Mechanistic data obtained thus far point to a cooperative bimetallic mechanism for nucleophile and electrophile activation.

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History

  • Published In Issue April 16, 2003
  • Received February 12, 2003

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