Chromium-catalyzed homoaldol equivalent reaction employing a nucleophilic propenyl acetate.
A scalable, highly regioselective chromium-catalyzed homoaldol equivalent reaction employing 3-bromopropenyl acetate as a masked homoenolate nucleophile in additions to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes under mild Cr/Mn redox conditions in good to excellent yields is reported. The resulting vinyl acetate-containing adducts are easily hydrolyzed with mild base to provide formal homoaldol adducts, or transformed to other more functionalized products by stereoselective transformations including epoxidation and cyclopropanation.
Kang
Jun Yong
JY
Texas A&M University, Department of Chemistry, P.O. Box 30012, College Station, Texas 77842-3012, USA.
Connell
Brian T
BT