Asymmetric synthesis of optically active fluorine-containing alcohols by the catalytic enantioselective alkylation of aldehydes

Abstract

Optically active fluorine-containing alcohols with up to 97% enantiomeric excess were synthesized by the enantioselective addition of dialkylzincs to fluorine-containing aldehydes using chiral β-aminoalcohol catalysts such as N,N-dibutylnorephedrine (DBNE, 2d), 2-morpholino-1-phenyl-1-propanol ( 2g, MOPEP) and diphenyl(1-methylpyrrolidin-2-yl)methanol ( 3, DPMPM).