Induction of asymmetry on the [4+3] cycloaddition reaction of C2-functionalized furans

被引：24
|
作者：
Montaña, AM [1 ]
Grima, PM [1 ]
机构：
[1] Univ Barcelona, Dept Quim Organ, Barcelona 08028, Spain
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 11期
关键词：
4+3]-cycloaddition; oxyallyl cation; syn-anti; endo exo; pi-facial diastereoselectivity; chiral auxiliary; furan;
D O I：
10.1016/S0040-4039(02)00199-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A study of the induction of asymmetry on the [4+3] cycloaddition reaction of some 13 C2-substituted furan derivatives with 2-oxyallyl cation is presented. The asymmetry was induced by a chiral auxiliary on C2 of furan. A vis diastereospecificity and a high endo diastereoselectivity are observed in almost all studied cases. On decreasing the distance between the stereocenter of the chiral auxiliary and the reactive C2-carbon of the furan ring, the pi-facial diastereoselectivity is increased. especially by using chiral furyl-sulfoxides. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2017 / 2021
页数：5
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