Silver-catalyzed asymmetric Sakurai-Hosomi allylation of ketones

ORGN 27

Manabu Wadamoto, m-wadamoto@northwestern.edu, Department of Chemistry, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208 and Hisashi Yamamoto, yamamoto@uchicago.edu, Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637.
The complex of AgF and (R)-DIFLUORPHOS has been shown an effective catalyst for the asymmetric Sakurai-Hosomi allylation of simple ketones. This catalyst system can be applied various simple ketones and corresponding tertiary homoallylic alcohols were obtained with excellent enantioselectivities (up to 96% ee). Only 1,2-adducts were obtained from both acyclic and cyclic conjugate ketones. The regio-, diastereo- and enantioselective crotylation has also been achieved. E or Z crotyltrimethoxysilane gave similar diastereomer ratio with high enantioselectivities.

 

Asymmetric Reactions and Syntheses
8:00 AM-11:40 AM, Sunday, 26 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006