Design of Chiral Catalysis and Asymmetric Autocatalysis for the Enantioselective Additions of Organozinc Reagents

Abstract

Diphenyl(1-methylpyrrolidin-2-yl)methanol (DPMPM) and N, N-dibutylnorephedrine (DBNE) are highly enantio- and chemoselective chiral catalysts for the addition of dialkylzincs to various aldehydes, affording sec-alcohols with high enantiomeric excesses. Heterogeneous chiral catalyst supported on polystyrene is also highly enantioselective. Pyrimidyl and quinolyl alkanols are asymmetric autocatalysts with amplification of enantiomeric excess in the enantioselective isopropylation of aldehydes. Enantioselective addition of dialkylzincs to N-diphenylphosphinylimines and conjugate addition to enones are performed using N, N-dialkylnorephedrines.