12-08

Enantioselective organocatalytic thiol addition to α,β-unsaturated α-amino acid derivatives, Synlett 23 (2012) 2195-2200

A.C. Breman, J.M.M. Smits, R. de Gelder, J.H. van Maarseveen, S. Ingemann and H. Hiemstra

Abstract: A new class of Michael acceptors based on α,β-unsaturated amino acids has been prepared and applied in asymmetric organocatalysis. With the use of thiourea derivatives of cinchona alkaloid-derived catalysts, efficient addition of thiols to the dehydroamino acids occurred with formation of β-thiol functionalized α-amino acids in high yields, moderate diastereoselectivities and ee values up to 95%.