Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins

Org Lett. 2007 Mar 15;9(6):1117-9. doi: 10.1021/ol070082x. Epub 2007 Feb 23.

Abstract

A chiral diamine was found to catalyze enantioselective addition of ketones to nitroolefins in aqueous/saline/organic media. The products were obtained with excellent diastereoselectivities (syn/anti = 99:1) and enantioselectivities up to 99%. The reaction could be facilitated using a mild acid. [reaction: see text]