Highly Diastereoselective Synthesis of Homoallylic Alcohols Bearing Adjacent Quaternary Centers Using Substituted Allylic Zinc Reagents

Hongjun Ren, Guillaume Dunet, Peter Mayer, and Paul Knochel*
Department Chemie und Biochemie, Ludwig-Maximilians-Universitt Mnchen, Butenandtstrasse 5-13, Haus F, 81377 Mnchen, Germany
J. Am. Chem. Soc., 2007, 129 (17), pp 5376–5377
DOI: 10.1021/ja071380s
Publication Date (Web): April 5, 2007
Copyright © 2007 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.

, paul.knochel@cup.uni-muenchen.de

Abstract

Abstract Image

Staring from readily available polysubstituted allylic chlorides, a range of polysubstituted allylic zinc chlorides were obtained using a LiCl-mediated zinc dust insertion in 55−84% yield. A highly diastereoselective synthesis of homoallylic alcohols bearing up to two adjacent quaternary centers was achieved using these polysubstituted allylic zinc reagents.

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History

  • Published In Issue May 02, 2007
  • Received March 2, 2007

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