Catalytic Enantioselective Alkylations of Tetrasubstituted Olefins. Synthesis of All-Carbon Quaternary Stereogenic Centers through Cu-Catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Enones

Alexander W. Hird and Amir H. Hoveyda*
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467
J. Am. Chem. Soc., 2005, 127 (43), pp 14988–14989
DOI: 10.1021/ja0553811
Publication Date (Web): October 7, 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.

, amir.hoveyda@bc.edu

Abstract

Abstract Image

A method for Cu-catalyzed asymmetric conjugate addition (ACA) of dialkylzinc reagents to tetrasubstituted five- and six-membered cyclic enones that afford quaternary all-carbon stereogenic centers in up to 95% ee is reported. Catalytic ACAs are practical and efficient. Reactions proceed to >98% conversion in undistilled commercial grade toluene in the presence of 2 mol % of an air-stable Cu salt (CuCN) and a readily available chiral ligand. Enantioselective ACA reactions deliver products that can be readily functionalized to afford a variety of synthetically versatile compounds in high optical purity.

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History

  • Published In Issue November 02, 2005
  • Received August 12, 2005

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