Artículos de revistas
Diastereoselective Addition of Arylzinc Reagents to Sugar Aldehydes
Fecha
2012Registro en:
ORGANIC LETTERS, WASHINGTON, v. 14, n. 15, pp. 3962-3965, AUG 3, 2012
1523-7060
10.1021/ol301724x
Autor
Wouters, Ana D.
Luedtke, Diogo S.
Institución
Resumen
The diastereoselective arylation of sugar-derived aldehydes is described. The arylating reagents are generated in situ by a boron-to-zinc exchange reaction of arylboronic acids with Et2Zn to generate arylethylzinc reagents. The exquisite reactivity of the arylzinc reagents allowed for an efficient and mild arylation, delivering the corresponding products in diastereolsomeric ratios of up to >20:1. The utility of the methodology is highlighted with an efficient formal synthesis of (+)-7-epl-goniofufurone, a member of the styryllactone family of natural products.