Asymmetric synthesis of chromanes via intramolecular indium-mediated allylation of hydrazones

ORGN 316

Gregory R. Cook, Gregory.Cook@ndsu.edu, Debasis Samanta, debasis.samanta@ndsu.edu, and Robert Kargbo, robert.kargbo@ndsu.edu. Department of Chemistry and Molecular Biology, North Dakota State University, 1231 Albrecht Avenue, P.O. Box 5516, Fargo, ND 58105-5516
We have recently reported the highly diastereoselective intermolecular allylation of chiral hydrazones utilizing allyl indium. The highly enantioselective catalytic reaction has also been accomplished by employing chiral BINOL derivatives as chiral additive. In pursuit of an efficient and asymmetric synthesis of chromane antibiotics, we have investigated the intramolecular variant of this reaction. Excellent yields and complete diastereocontrol has been accomplished in the presence of protic acid additives. We will present our recent findings on the role of the additive as well as extension to the enantioselective reaction.

 

Metal-Mediated Reactions and Syntheses
1:00 PM-5:00 PM, Monday, 11 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

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