Cyclopentyl and carbohydrate derivatives of N-hydroxy-4-methylthiazole-2(3H)-thione: Synthesis by Mitsunobu reaction and highly selective photochemical conversion into aldehydes

Article abstract of DOI:10.1055/s-2001-14598

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 mannose in the presence of PPh ₃, diethyl azodicarboxylate (DEAD), and N-hydroxy-4-methylthiazole-2(3H)-thione (1). Alkoxyl radical precursors 3 were photoreacted with hydrogen atom donors to afford substituted aldehydes 7 or formyl esters 10-11 via highly regioselective alkoxyl radical fragmentations.