Abstract
Previous research in the Krauss lab allowed for homoallylboration and homocrotylboration of aldehydes using a stoichiometric amount of the Lewis acid promoter PhBCl2. More recently, a boron carboxylate catalyst has been discovered for this reaction. Screening of boron carboxylates formed from the coupling of borane with various carboxylic acids has led to the establishment of a structure-activity relationship. Within the series of simple monocyclic aryl carboxylates, only those derived from electron poor carboxylic acids can successfully catalyze the homoallylation of aldehydes. A chiral carboxylic acid derived from (R)-(+)-1,1′-Bi(2-naphthol), (BINOL), has been synthesized. Efforts to couple this chiral acid to borane as well as the synthesis of other chiral acids will be continued.