The enantioselective Diels-Alder reaction of 1-methoxybuta-1,3-diene with n-butyl glyoxylate catalyzed by Jacobsen's chromium complexes

被引：16

作者：

Kwiatkowski, P

Asztemborska, M

Jurczaka, J

机构：

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

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

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

来源：

SYNLETT | 2004年 / 10期

关键词：

asymmetric catalysis; chromium(III); Diels-Alder reaction; salen complexes; stereoselectivity;

D O I：

10.1055/s-2004-829055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hetero-Diels-Alder reaction of 1-methoxybuta-1,3-diene (1) with n-butyl glyoxylate (2), catalyzed by chiral chromium(III) complexes 4-6 (2 mol%), afforded the [4+2]cycloadducts 3 in good yields (up to 96%), diastereoselectivity (up to 86% de), and enantioselectivity (up to 88% ee). Our approach opens an easy access to the synthetically important 6-substituted 2-methoxy-5,6-dihydro-2H-pyrans of type 3.

引用

页码：1755 / 1758

页数：4

共 34 条

[1] [Cr(Salen)] as a 'bridge' between asymmetric catalysis, Lewis acids and redox processes [J].