Synfacts 2005(0): 0053-0053  
DOI: 10.1055/s-2005-869916
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Synthesis of Chiral Allylic Esters

Contributor(s): Hisashi Yamamoto, Matthew Boxer
S. F. Kirsch, L. E. Overman*
University of California, Irvine, USA
Catalytic Asymmetric Synthesis of Chiral Allylic Esters
J. Am. Chem. Soc.  2005,  127:  2866-2867  
Further Information

Publication History

Publication Date:
20 July 2005 (online)


Significance

The conversion of Z-allylic alcohols to trichloroacetamide derivatives allows for the formation of highly enantioenriched allylic esters through this palladium-catalyzed pathway. This is the first catalytic asymmetric allylic esterification. The starting trichloroacetimidates can be prepared quite simply from allylic alcohols and trichloroacetonitrile.

Comment

Allylic esters and alcohols are both common and important functionalities in biologically active compounds. Chiral allylic alcohols and their derivatives (such as esters) are often prepared through kinetic resolution of the alcohol. This is a superior alternative that provides high yields and ee’s utilizing full molar quantities of starting materials with only catalytic amounts of a chiral source, and furnishes the ester directly.