Sequential Catalytic Isomerization and Allylic Substitution. Conversion of Racemic Branched Allylic Carbonates to Enantioenriched Allylic Substitution Products

Shashank Shekhar, Brian Trantow, Andreas Leitner, and John F. Hartwig*
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107
J. Am. Chem. Soc., 2006, 128 (36), pp 11770–11771
DOI: 10.1021/ja0644273
Publication Date (Web): August 19, 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.

, john.hartwig@yale.edu

Abstract

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A catalytic protocol for the conversion of readily accessible racemic, branched aromatic allylic esters to branched allylic amines, ethers, and alkyls has been developed. Palladium-catalyzed isomerization of branched allylic esters to terminal allylic esters, followed by sequential iridium-catalyzed allylic substitution, gave the branched allylic products in good yield with high regioisomeric and enantiomeric selectivity. Both electron-rich and electron-poor branched allylic esters gave products in >90% ee. High enantiomeric excesses were also observed for the products from the reactions of 2-thienyl acetates and dienyl carbonates.

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History

  • Published In Issue September 13, 2006
  • Received June 22, 2006

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