Asymmetric Morita−Baylis−Hillman Reactions Catalyzed by Chiral Brønsted Acids

Nolan T. McDougal and Scott E. Schaus*
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215
J. Am. Chem. Soc., 2003, 125 (40), pp 12094–12095
DOI: 10.1021/ja037705w
Publication Date (Web): September 12, 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.

, seschaus@chem.bu.edu

Abstract

Abstract Image

Chiral BINOL-derived Brønsted acids catalyze the enantioselective asymmetric Morita−Baylis−Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2−20 mol % of the chiral Brønsted acid 2e or 2f and triethylphosphine as the nucleophilic promoter. The reaction products are obtained in good yields (39−88%) and high enantioselectivities (67−96% ee). The Brønsted-acid-catalyzed reaction is the first example of a highly enantioselective asymmetric MBH reaction of cyclohexenone with aldehydes.

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History

  • Published In Issue October 08, 2003
  • Received August 1, 2003

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