Synthesis and Lewis acid catalyzed Claisen rearrangement of 2-(1,3-oxazolin-2-yl)-substituted allyl vinyl ethers

被引：24

作者：

Helmboldt, H ^{[1
]}

Hiersemann, M ^{[1
]}

机构：

[1] Tech Univ Dresden, Inst Organ Chem, D-01069 Dresden, Germany

来源：

TETRAHEDRON | 2003年 / 59卷 / 23期

关键词：

Claisen rearrangement; catalysis; Lewis acid; copper(II)bis(oxazoline); allyl vinyl ether;

D O I：

10.1016/S0040-4020(03)00590-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allyl vinyl ethers containing an acceptor function in the 2-position are useful substrates for the Lewis acid-catalyzed Claisen rearrangement. The first synthesis of acyclic 2-(1,3-oxazolin-2-yl)-substituted allyl vinyl ethers is reported. The Lewis acid catalyzed Claisen rearrangement of these allyl vinyl ethers afforded the rearrangement products with low to moderate diastereo- and enantioselectivity. The catalyzed rearrangement of chiral allyl vinyl ethers was investigated. The combination of substrate- and catalyst-induced diastereoselectivity led to unexpected and unprecedented results. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：4031 / 4038

页数：8

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