Palladium-Catalyzed Enantioselective Diboration of Prochiral Allenes

Nicholas F. Pelz, Angela R. Woodward, Heather E. Burks, Joshua D. Sieber, and James P. Morken*
Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina, Chapel Hill, North Carolina 27599-3290
J. Am. Chem. Soc., 2004, 126 (50), pp 16328–16329
DOI: 10.1021/ja044167u
Publication Date (Web): November 24, 2004
Copyright © 2004 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

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Pd-catalyzed diboration of prochiral allenes occurs exclusively at the internal position and is remarkably accelerated in the presence of Lewis basic ligand structures. On the basis of preliminary observations, a chiral ligand was employed, and the enantiomeric excess of a variety of diboration products was found to be in the range of 86−92% ee. The chiral diboron reaction products should be useful in organic synthesis, and preliminary experiments suggest that they may participate in allylation reactions with a high level of chirality transfer.

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History

  • Published In Issue December 22, 2004
  • Received September 25, 2004

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