THE ENOLATE GROUP AS DIPOLAROPHILE IN INTRAMOLECULAR CYCLOADDITION OF NITRONES

被引：12

作者：

AURICH, HG

KOSTER, H

机构：

[1] Fachbereich Chemie der Philipps-Universität Marburg

来源：

TETRAHEDRON | 1995年 / 51卷 / 22期

关键词：

D O I：

10.1016/0040-4020(95)00283-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrones 5 were prepared starting from N-benzylalaninol 3. Michael addition of 3 to 3-butenone-2 afforded alcohol 4 which was converted to 5 by Swern oxidation and subsequent treatment of the resulting aldehyde with N-alkylhydroxylamines. The enolate group of nitrones 6 generated by treatment of 5 with LDA acted as dipolarophile attacking the nitrone group to give the bicyclic compounds 7 by a spontaneous intramolecular cycloaddition. This took place with high diastereoselectivity affording only one diastereomer in 23 to 65% yield. The two substituents at position 4 give rise to a change in conformation of compounds 7 compared to compounds 8 unsubstituted at this position.

引用

页码：6285 / 6292

页数：8

共 24 条

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