Sequential Pd-Catalyzed Asymmetric Allene Diboration/α-Aminoallylation

Joshua D. Sieber and James P. Morken*
Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290
J. Am. Chem. Soc., 2006, 128 (1), pp 74–75
DOI: 10.1021/ja057020r
Publication Date (Web): December 7, 2005
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.

, morken@unc.edu

Abstract

Abstract Image

Pd-catalyzed enantioselective diboration of prochiral allenes provides adducts which participate in highly selective allylation reactions with primary imines. The allylation product is a vinyl boronate which may be oxidized to give nonracemic Mannich products (87−97% ee). Alternatively, enantiomerically enriched homoallylic amine derivatives may be obtained by protonation and Suzuki cross-coupling of the vinyl boronate.

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History

  • Published In Issue January 11, 2006
  • Received October 21, 2005

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