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
收藏
页码：4031 / 4038
页数：8
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