Stereoselective Synthesis of anti-α-(Difluoromethyl)-β-amino Alcohols by Boronic Acid Based Three-Component Condensation. Stereoselective Preparation of (2S,3R)-Difluorothreonine

G. K. Surya Prakash,* Mihirbaran Mandal, Stefan Schweizer, Nicos A. Petasis,* and George A. Olah*
Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, California 90089-1661
J. Org. Chem., 2002, 67 (11), pp 3718–3723
DOI: 10.1021/jo011116w
Publication Date (Web): April 27, 2002
Copyright © 2002 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.

, gprakash@.usc.edu

Abstract

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Starting from optically active 3,3-difluorolactaldehyde, an alkenyl or aryl boronic acid, and an amine, a one-step three-component methodology was developed for the stereoselective preparation of anti-α-(difluoromethyl)-β-amino alcohols. β-Furyl-substituted anti-α-(difluoromethyl)-β-amino alcohol was further elaborated to form (2S,3R)-difluorothreonine in high yield and ee.

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History

  • Published In Issue May 31, 2002
  • Received December 3, 2001

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