Photoreactions of N-alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones with l-cysteine derivatives in aqueous solutions

Abstract

Photolysis of substituted N-alkoxythiazolethiones 1 in aqueous solvents furnishes alkoxyl radicals 2, which, upon stereoselective 5-exo-trig cyclization, are trapped by water soluble thiols (L-cysteine, L-cysteine ethyl ester, or the reduced form of glutathione, GSH) to afford disubstituted tetrahydrofurans 3 in synthetically useful yields and with satisfactory to excellent diastereoselectivities.