Hydroxy-Directed, SmI(2)-Induced Conversion of Carbohydrates into Carbocycles.
Angew Chem Int Ed Engl
; 39(2): 355-357, 2000 Jan.
Article
en En
| MEDLINE
| ID: mdl-10649407
Polyoxygenated six-membered carbocycles were derived from carbohydrates with complete stereocontrol through hydroxy-directed coupling cyclization induced by SmI(2). For example, the cis-1,3-cyclohexanediol 3 is obtained from the D-glucopyranoside derivative 1 in excellent yield. The coupling cyclization is initiated by single-electron transfer from SmI(2) to the formyl group of the delta-hydroxy aldehyde 2 generated in an equilibrium process.
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01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2000
Tipo del documento:
Article
Pais de publicación:
Alemania