Synthesis and evaluation of guanidinyl pyrrolidines as bifunctional catalysts for enantioselective conjugate additions to cyclic enones

Org Biomol Chem. 2009 Jan 21;7(2):319-24. doi: 10.1039/b812038b. Epub 2008 Nov 17.

Abstract

Guanidinyl pyrrolidines derived from 'S'-proline are effective catalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cyclohexenone and cyclopentenone in the absence of basic additives. The stereoselectivity is strongly dependent on catalyst loading as well as reaction concentration.