New chiral selenium electrophiles derived from functionalized terpenes

被引：18

作者：

Scianowski, Jacek ^{[1
]}

Rafinski, Zbigniew ^{[1
]}

Szuniewicz, Aleksandra ^{[1
]}

Wojtczak, Andrzej ^{[2
]}

机构：

[1] Nicholas Copernicus Univ, Dept Organ Chem, PL-87100 Torun, Poland

[2] Nicholas Copernicus Univ, Dept Crystallochem & Biocrystallog, PL-87100 Torun, Poland

来源：

TETRAHEDRON | 2009年 / 65卷 / 49期

关键词：

Terpenoids; Diselenides; Asymmetric synthesis; Selenenylation reaction; ASYMMETRIC ADDITION-REACTIONS; DIALKYL DISELENIDES; ORGANIC-COMPOUNDS; NITROGEN ATOM; METHOXYSELENENYLATIONS; DIETHYLZINC; CATALYSTS;

D O I：

10.1016/j.tet.2009.10.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient method for the synthesis of optically active dialkyl diselenides derived from bicyclic terpenes functionalized with hydroxy, etheral. sulfide, and selenide groups is described. The diselenides were used for a synthesis of chiral electrophilic selenium reagents, then in the asymmetric selenenylation of styrene and selenocyclization with o-allylphenol. The influence of nonbonding selenium-heteroatom interactions in the generated organoselenium electrophiles on the stereo-selectivity of an addition reaction has been investigated. Calculations by a DFT method on a B3LYP (6-311G (d)) level, confirmed the existence of nonbonded selenium-heteroatom interactions in the investigated systems. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：10162 / 10174

页数：13

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