Direct carbohydrate to carbocycle conversions via intramolecular allylation with Et2Zn/Pd(0)

被引：13

作者：

Aurrecoechea, JM ^{[1
]}

Arrate, M ^{[1
]}

Gil, JH ^{[1
]}

López, B ^{[1
]}

机构：

[1] Univ Basque Country, Fac Ciencias, Dept Quim Organ 2, E-48080 Bilbao, Spain

来源：

TETRAHEDRON | 2003年 / 59卷 / 29期

关键词：

allylations; carbohydrates; cyclizations; palladium; zinc;

D O I：

10.1016/S0040-4020(03)00825-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 5-vinylpyranosides with Et2Zn and catalytic Pd(0), in the presence of ZnCl2, results in the formation of 5-membered carbocyclic products. This carbohydrate ring-contraction features an intramolecular allylation of a ring-opened carbohydrate aldehyde by an in situ-generated nucleophilic allylzinc species. The stereoselectivity about vinyl and free hydroxyl groups at the newly created stereogenic centers varies from low to moderate while both its extent and sense are found to depend on particular structural features (e.g. the configuration of the starting carbohydrate). (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：5515 / 5522

页数：8

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