Catalytic enantioselective addition of thioacids to trisubstituted nitroalkenes

Angew Chem Int Ed Engl. 2014 Oct 13;53(42):11329-32. doi: 10.1002/anie.201406971. Epub 2014 Sep 4.

Abstract

The first example of a catalytic enantioselective addition to and nitronate protonation of trisubstituted nitroalkenes to produce highly enantioenriched products with a tetrasubstituted carbon is reported. Thioacids added in excellent yields and with high enantioselectivities to both activated and unactivated nitroalkenes. The 1,2-nitrothioacetate products can be readily converted in two steps to biomedically relevant 1,2-aminosulfonic acids without loss of enantiopurity.

Keywords: asymmetric catalysis; michael addition; nitroalkene; organocatalysis.