title: Chiral boronate derivatives via catalytic enantioselective conjugate addition of Grignard reagents on 3-boronyl unsaturated esters and thioesters.
abstract: There is a growing interest in the development of new methods to prepare chiral organoboronate derivatives in optically pure form. An efficient copper-catalyzed enantioselective conjugate addition methodology using Grignard reagents and 3-boronyl acrylate derivatives was optimized for the preparation of chiral alkylboronate products in high yields and up to 98% ee. The resulting 1,8-diaminonaphthalene adducts can be transformed into the corresponding boronic acid, pinacol boronate, and trifluoroborate salt. This method extends the realm of chemical reactions compatible with useful boron-containing substrates.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, AB, T6G 2G2, Canada.
authors.forename: Jack Chang Hung
authors.initials: JC
authors.lastname: Lee
authors.forename: Dennis G
authors.initials: DG
authors.lastname: Hall