The high-pressure [4+2]cyclo addition of 1-methoxybuta-1,3-diene to the glycolaldehyde-derived heterodienophiles, catalyzed by chiral metallosalen complexes

被引：17

作者：

Kwiatkowski, P

Chaladaj, W

Malinowska, M

Asztemborska, M

Jurczak, J ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Warsaw Univ, Dept Chem, PL-02093 Warsaw, Poland

[3] Polish Acad Sci, Inst Phys Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 17期

关键词：

D O I：

10.1016/j.tetasy.2005.07.031

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A high-pressure (ca. 10 kbar) reaction of 1-methoxybuta-1,3-diene 1 with variously O-protected glycolaidehydes 2, catalyzed by the chiral (salen)Cr(III)Cl 4a-d and 5 or (salen)Co(II) 6a-f and 7 complexes, has been studied. The best results were obtained for tert-butyldimethylsilyloxyacetaldehyde 2a. The reaction afforded, in good yield (up to 90%) and with very good diastereoselectivity (up to 92%) and enantioselectivity (up to 93% ee), the [4+2]cycloadducts 3a, which are compounds of significant synthetic interest. The stereochemical model of the cycloaddition reaction is discussed. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2959 / 2964

页数：6

共 36 条

[11] ASYMMETRIC HETERO-DIELS-ALDER REACTIONS AND ENE REACTIONS CATALYZED BY CHIRAL COPPER(II) COMPLEXES [J].