Cyclopentyl and carbohydrate derivatives of N-hydroxy-4-methyl-thiazole-2(3H)-thione: Synthesis by Mitsunobu reaction and highly selective photochemical conversion into aldehydes
J. Hartung et al., Cyclopentyl and carbohydrate derivatives of N-hydroxy-4-methyl-thiazole-2(3H)-thione: Synthesis by Mitsunobu reaction and highly selective photochemical conversion into aldehydes, SYNLETT, (6), 2001, pp. 749-752
Substituted N-cyclopentoxy- and carbohydrate-derived thiazole-2(3H)-thiones
3 were prepared from alcohols 2 or from 2,3:5,6-di-O-isopropylidene mannos
e in the presence of PPh3, diethyl azodicarboxylate (DEAD), and N-hydroxy-4
-methylthiazole-2(3H)-thione (1). Alkoxyl radical precursors 3 were photore
acted with hydrogen atom donors to afford substituted aldehydes 7 or formyl
esters 10-11 via highly regioselective alkoxyl radical fragmentations.