Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles

Tetrahedron Lett. 2010 Mar 3;51(9):1322. doi: 10.1016/j.tetlet.2009.12.139.

Abstract

2-Amino-8-oxo-tetrahydro-4H-chromene-3-carbonitriles were synthesized for the first time from a tandem Michael addition - cyclization reaction between cyclohexane-1,2-dione and benzylidenemalononitriles. An enantioselective synthesis of these compounds was achieved in moderate ee values (up to 63% ee) by using a cinchona alkaloid-derived thiouea catalyst.