Chiral cations in 4+3 cycloadditions

被引：32

作者：

Harmata, M ^{[1
]}

Jones, DE ^{[1
]}

Kahraman, M ^{[1
]}

Sharma, U ^{[1
]}

Barnes, CL ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(99)00080-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the chiral acetal 4 with furan and cyclopentadiene in the presence of a Lewis acid gives 4+3 cycloadducts in very good yields. Diastereoselectivity in the case of furan is exceptionally high, while that for the reaction with cyclopentadiene is lower. The sense of diastereoselection in the case of furan is opposite to that which would be predicted on the basis of mechanistic models for the origin of stereoselectivity in many reactions of chiral acetals mediated by Lewis acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1831 / 1834

页数：4

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