High-pressure and thermally induced intramolecular Diels-Alder reactions of furfuryl fumarates. Influence of tether substituents on diastereoselectivity

被引：18

作者：

Butz, T ^{[1
]}

Sauer, J ^{[1
]}

机构：

[1] UNIV REGENSBURG,INST ORGAN CHEM,D-93040 REGENSBURG,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(97)00015-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric intramolecular Diels-Alder (IMDA) reactions of optically active furfuryl fumarates result after crystallization in enantiopure 7-oxabicyclo[2.2.1]heptene derivatives that may be useful building blocks for natural product synthesis. The influence of high-pressure and thermal activation has been studied for these cycloadditions. The diastereoselectivities observed increase with the size of the tether substituents, but not linearly. A possible explanation based on transannular interactions is given. (C) 1997 Elsevier Science Ltd.

引用

页码：703 / 714

页数：12

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