Synthesis of oxygen heterocycles via Pd-catalyzed olefin carboetherifcation

ORGN 266

Michael B. Hay, haym@umich.edu and John P. Wolfe, jpwolfe@umich.edu. Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI 48109-1055
An efficient protocol for the synthesis of oxygen containing heterocycles from gamma hydroxy olefin derivatives and aryl or vinyl bromides has been developed. This methodology allows for the diastereoselective construction of 2-benzyl- and 2-allyltetrahydrofurans via palladium catalyzed olefin carboetherification. The extension of this methodology toward the construction of other oxygen containing heterocycles will be described. Reaction scope, mechanism, and diastereoselectivity trends will also be discussed.
 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 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