SYNTHESIS OF CHIRAL AMINOCYCLITOLS VIA EPOXYEPIMINATION

被引：31

作者：

BRAUN, H ^{[1
]}

BURGER, W ^{[1
]}

KRESZE, G ^{[1
]}

SCHMIDTCHEN, FP ^{[1
]}

VAERMAN, JL ^{[1
]}

VIEHE, HG ^{[1
]}

机构：

[1] UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN LAB,B-1348 LOUVAIN,BELGIUM

来源：

TETRAHEDRON-ASYMMETRY | 1990年 / 1卷 / 06期

关键词：

D O I：

10.1016/0957-4166(90)90041-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric Hetero-Diels-Alder reactions of cyclohexadienes 1 and (±)2 with the α-chloronitroso derivative of D-mannose 6 give the chiral dihydrooxazines 3-5. After N-functionalisation with the chloro-olefin 10 the N-vinyl-dihydrooxazines 11-13 thermally rearrange to epoxyepimines 14-16. The formation of konduramine byproducts 18 and 19 indicates a biradical mechanism. Opening of oxirane and aziridine rings of 14 and acidic enamine hydrolysis lead to chiral aminocyclitols. © 1990.

引用

页码：403 / 415

页数：13

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