A New Family of Cinchona-Derived Amino Phosphine Precatalysts: Application to the Highly Enantio- and Diastereoselective Silver-Catalyzed Isocyanoacetate Aldol Reaction

摘要

A new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epi-cinchona alkaloids has been developed. In combination with Ag(Ⅰ) salts, these amino-phosphines performed as effective cooperative Bronsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained.