title: Chromium-catalyzed homoaldol equivalent reaction employing a nucleophilic propenyl acetate.
abstract: 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.
authors.affiliation: Texas A&M University, Department of Chemistry, P.O. Box 30012, College Station, Texas 77842-3012, USA.
authors.forename: Jun Yong
authors.initials: JY
authors.lastname: Kang
authors.forename: Brian T
authors.initials: BT
authors.lastname: Connell