Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction

ORGN 29

Qin Liu, diqin77@lamar.colostate.edu and Tomislav Rovis, rovis@lamar.colostate.edu. Department of Chemistry, Colorado State University, Fort Collins, CO 80523
Dearomatization of phenols followed by oxidation affords cyclohexadienyloxyacetaldehydes, which produce hydrobenzofuranones via asymmetric intramolecular Stetter reaction in good to excellent yield. Quaternary stereocenter and up to three contiguous stereocenters may be formed in good to excellent enantioselectivities and excellent diastereoselectivities.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:20 PM, Sunday, 10 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006