Palladium-Catalyzed C(sp3)–C(sp2) Cross-Couplings of O-(α-Bromoacyl) Cyanohydrins with Boronic Acids: An Entry to Enantio­enriched N-Acylated β-Amino Alcohols

Abstract

Suzuki-type cross-coupling of enantiomerically enriched O-(α-bromoacyl) cyanohydrins with aromatic boronic acids substituted with electron-withdrawing or electron-donating groups gave the expected coupling products in high yields without racemization. These substrates exhibit higher reactivities than analogous substrates lacking the nitrile function, probably as a result of π-coordination of the nitrile to palladium. Reduction of the nitrile group of the products, with accompanying intramolecular acyl transfer, provides access to biologically interesting N-acylated β-amino alcohols.