Silver fluoride-catalyzed enantioselective Mukaiyama aldol additions to ketones

ORGN 26

Laura C. Akullian, Marc L. Snapper, and Amir H. Hoveyda. Department of Chemistry, Boston College, Merkert Center, 2609 Beacon St., Chestnut Hill, MA 02467
A new and efficient catalytic method for addition of enolsilanes to ketones has been developed. Reactions are promoted by silver fluoride salts in the presence of accessible, modular peptide ligands. Catalytic asymmetric aldol additions deliver the desired tertiary alcohols in up to 96% ee and >90% isolated yield. Notable aspects of screening studies leading to optimal catalysts, the scope and limitations of this method and related mechanistic insights, as well as applications to target oriented synthesis will be presented.

 

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