Formation of enantiopure tricyclic compounds by intramolecular 1,3-dipolar cycloaddition of nitrones

被引：13

作者：

Aurich, HG ^{[1
]}

Geiger, M ^{[1
]}

Gentes, C ^{[1
]}

Harms, K ^{[1
]}

Köster, H ^{[1
]}

机构：

[1] Univ Marburg, Fac Chem, D-35032 Marburg, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 13期

关键词：

D O I：

10.1016/S0040-4020(98)00064-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitrones 6 prepared from ester 5 underwent an intramolecular cycloaddition affording diastereomeric mixtures of tricyclic compounds 7A/B. These were separated to give the enantiopure compounds 7A and 7B. Starting from aminoalcohol 8 compounds 10A and 10B were formed via nitrones 9. Nitrone 9a yielded the trans-product 10aC in addition. X-ray analyses confirm the structure of 7aB and 10aA. Catalytic hydrogenation of compounds 7A and 7B yielded the bicyclic gamma-aminoalcohols, which were tested as ligands in the enantioselective addition of diethylzinc to benzaldehyde. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3181 / 3196

页数：16

共 20 条

[1]

AEURICH HG, 1997, SYNLETT, P1004

[2] Formation of non-racemic tricyclic compounds by intramolecular 1,3-dipolar cycloaddition of nitrones [J].