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
收藏
页码：3181 / 3196
页数：16
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