Chemical Communications

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

J Hartung, R Kneuer, K Špehar

Index: Hartung; Kneuer; Spehar Chemical Communications, 2001 , # 9 p. 799 - 800

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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.

~44%

~20%

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