Enantioselective synthesis of alpha-tertiary hydroxyl aldehydes by palladium-catalyzed asymmetric allylic alkylation of enolates

ORGN 127

Barry Trost, bmtrost@stanford.edu, Jiayi Xu, xujiayi@stanford.edu, and Markus Reichle, reichle@stanford.edu. Department of Chemistry, Stanford University, Stanford, CA 94305
We have previously reported the palladium catalyzed asymmetric allylic alkylation of ketone enolates to generate ketones with either an α-tertiary or quaternary center. Herein, we report a highly diastereo-and enantioselective strategy to synthesize α-tertiary hydroxyl aldehydes and its application in the short synthesis of oxybutynin. The detailed reaction scope and further applications with be discussed.

 

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