Electrophilic 5-endo-trig cyclisations of 2-silyl-3-alkenols. A stereoselective route to polysubstituted tetrahydrofurans.

被引：34

作者：

Andrey, O ^{[1
]}

Ducry, L ^{[1
]}

Landais, Y ^{[1
]}

Planchenault, D ^{[1
]}

Weber, V ^{[1
]}

机构：

[1] UNIV LAUSANNE,COLL PROPEDEUT,INST CHIM ORGAN,CH-1015 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON | 1997年 / 53卷 / 12期

关键词：

ALDOL-CYCLIZATION SEQUENCE; ALPHA-SILYLACETIC ESTERS; SUBSTITUTED TETRAHYDROFURANS; HOMOALLYLIC ALCOHOLS; ORGANIC-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; STEREOSPECIFIC SYNTHESIS; SILAFUNCTIONAL COMPOUNDS; ORGANOTIN COMPOUNDS; SILICON;

D O I：

10.1016/S0040-4020(97)00109-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic 5-endo-trig cyclisations of allylsilanes have been carried out leading to tri- and tetrasubstituted tetrahydrofurans with reasonable fields and excellent diastereoselectivities. A rationalization of both the regio- and the stereoselectivity has been proposed. A silicon group having a thienyl fragment attached to the silicon has also been devised was shown to be oxidized under both electrophilic and nucleophilic conditions. (C) 1997 Elsevier Science Ltd.

引用

页码：4339 / 4352

页数：14

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