A joint experimental and ab initio study on the reactivity of several hydroxy selenides.: Stereoselective synthesis of cis-disubstituted tetrahydrofurans via seleniranium ions

被引：22

作者：

Gruttadauria, M ^{[1
]}

Aprile, C ^{[1
]}

D'Anna, F ^{[1
]}

Lo Meo, P ^{[1
]}

Riela, S ^{[1
]}

Noto, R ^{[1
]}

机构：

[1] Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 31期

关键词：

cyclizations; oxygen heterocycles; selenium; theoretical studies;

D O I：

10.1016/S0040-4020(01)00618-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of several hydroxy selenides bearing an ethereal chain with catalytic amounts of perchloric acid in dichloromethane was investigated. Results showed that the position of the oxygen atom with respect to the seleniranium ring was crucial in order to aet a good yield of the cyclized product. The factors on which yields of the 5-endo cyclization of the seleniranium ions depend were analysed by ab initio (HF/3-21G*) studies. An explanation of the different coordinating ability, towards the positively charged selenium atom, of the allylic OMe and homoallylic OH-2 groups was given. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6815 / 6822

页数：8

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