trans-Hydroalumination/Alkylation:  One-Pot Synthesis of Trisubstituted Allylic Alcohols

Neil F. Langille and Timothy F. Jamison*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
Org. Lett., 2006, 8 (17), pp 3761–3764
DOI: 10.1021/ol0613721
Publication Date (Web): July 29, 2006
Copyright © 2006 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.

, tfj@mit.edu

Abstract

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Described herein is a method of stereoselective synthesis of trisubstituted allylic alcohols by alkylation of alkenyl alanates, formed in situ through treatment of propargyl alcohols with Vitride (Red-Al). This technique represents the first of its kind to feature a trans-hydrometalation, and is particularly effective for the formation of 1,4-dienes. Applications involving primary, secondary, and tertiary alcohols are discussed, as well as limitations regarding both alkyne and electrophile components.

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History

  • Published In Issue August 17, 2006
  • Received June 5, 2006

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