Stereoselective Olefin Isomerization Leading to Asymmetric Quaternary Carbon Construction

Kan Wang, Christopher J. Bungard, and Scott G. Nelson*
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260
Org. Lett., 2007, 9 (12), pp 2325–2328
DOI: 10.1021/ol0706511
Publication Date (Web): May 17, 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.

, sgnelson@pitt.edu

Abstract

Abstract Image

Chemo- and stereoselective Ir(I)-catalyzed isomerization of 1,1-disubstituted and trisubstituted allylic ethers and in situ [3,3] sigmatropic rearrangement of the resulting allyl vinyl ethers provide for the highly stereoselective construction of quaternary carbon stereocenters. The olefin isomerization−Claisen rearrangement (ICR) sequence allows adjacent quaternary−tertiary stereocenter relationships to be established with excellent diastereoselection. Several complementary strategies for enantioselective quaternary carbon synthesis derive directly from the ICR reaction design.

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History

  • Published In Issue June 07, 2007
  • Received March 21, 2007

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