Proline-catalyzed tandem aldol and alkylation reactions in alcoholic medium

ORGN 121

Cong-Gui Zhao, cong.zhao@utsa.edu, Dodda Rajasekhar, and Jinyun Liu. Department of Chemistry, University of Texas at San Antonio, 6900 N. Loop 1604 W, San Antonio, TX 78249-0698
Proline catalyzed aldol reaction of aldehyde and ketone in aprotic solvent and water generates the normal aldol product. However, when this reaction is carried out in an alcoholic medium, the aldol product is further alkylated by the alcohol to give β-alkoxyketone product in good yields. The mechanism and synthetic application of this new reaction will be discussed.