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

Citation
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
Citations number
27
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
0936-5214 → ACNP
Issue
6
Year of publication
2001
Pages
749 - 752
Database
ISI
SICI code
0936-5214(200106):6<749:CACDON>2.0.ZU;2-9
Abstract
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.