Novel catalytic approach to chiral lactones

ORGN 627

Zengming Shen, shenzengming@hotmail.com, Hasan Khan, hasnik@gmail.com, and Vy M. Dong, vdong@chem.utoronto.ca. Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S 3H6

Chiral lactones are important architectures found in a variety of macrolide antibiotic structures.  Traditional strategies for generating lactones rely on the coupling of alcohols and carboxylic acids using stoichiometric coupling reagents such as 2,4,6-trichlorobenzoyl chloride/DMAP, ethyl azodicarboxylate/PPh3, DCC and 2-halopyridinium salt.  This poster describes a catalytic and atom economical synthesis of lactones directly from aldehydes and ketones.  Our approach involves an unpredecedented reduction of ketones to generate chiral lactones in up to 99% ee.  The mechanism, scope, and limitations of this process will be discussed.