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

作者:Sladojevich Filippo; Trabocchi Andrea; Guarna Antonio; Dixon Darren J*
来源:Journal of the American Chemical Society, 2011, 133(6): 1710-1713.
DOI:10.1021/ja110534g

摘要

Anew class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epicinchona 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.

  • 出版日期2011-2-16