Asymmetric Synthesis of Protected Arylglycines by Rhodium-Catalyzed Addition of Arylboronic Acids to N-tert-Butanesulfinyl Imino Esters

Melissa A. Beenen, Daniel J. Weix, and Jonathan A. Ellman*
Department of Chemistry, University of California, Berkeley, California 94720
J. Am. Chem. Soc., 2006, 128 (19), pp 6304–6305
DOI: 10.1021/ja060529h
Publication Date (Web): April 25, 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.

, jellman@berkeley.edu

Abstract

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A new method for the Rh(I)-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters has been developed for the asymmetric synthesis of arylglycine derivatives. This method provides high yields (61−90%) and diastereoselectivities (>98:2) for a variety of functionalized arylboronic acids. The N-sulfinyl arylglycine ester products are versatile intermediates for further transformations, including selective protecting group removal, conversion to β-amino alcohols, and direct incorporation into peptides.

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History

  • Published In Issue May 17, 2006
  • Received January 23, 2006

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