Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters

ORGN 117

Melissa A. Beenen, mbeenen@berkeley.edu1, Daniel J. Weix, dan_weix@uclink.berkeley.edu1, and Jonathan A. Ellman, jellman@berkeley.edu2. (1) Department of Chemistry, University of California Berkeley, B84 Hildebrand, Berkeley, CA 94720-1460, (2) Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720
Arylglycines are components of a number of significant drugs, such as Plavix, one of the top grossing pharmaceuticals for 2005. As a result, the asymmetric synthesis of these compounds is an important goal in organic chemistry. Recently, much attention has been focused on metal-catalyzed additions of arylboronic acids to N-protected aryl or alkyl imines. Herein we report an efficient asymmetric synthesis of arylglycines based on a rhodium-catalyzed addition of arylboronic acids to N-sulfinyl iminoacetates. This method proceeds with high yields and high diastereoselectivities for a variety of electronically diverse substituted arylboronic acid derivatives. We have also demonstrated the utility of the subsequent protected arylglycine products by subjecting them to further synthetic transformations, including peptide coupling.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006