CYCLOADDITIONS OF 2-NITRO 1,3-DIENES TO ENAMINES - ASYMMETRIC INDUCTION AND SYNTHESIS OF UNSATURATED NITROKETONES AND DIELS-ALDER ADDUCTS VIA [4+2] HETEROCYCLOADDITIONS

被引：13
|
作者：
CHINCHILLA, R [1 ]
BACKVALL, JE [1 ]
机构：
[1] UNIV UPPSALA,DEPT ORGAN CHEM,S-75121 UPPSALA,SWEDEN
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 38期
关键词：
D O I：
10.1016/S0040-4039(00)61168-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Nitro 1,3-dienes, generated in situ from the corresponding nitroseleno compounds, react with enamines affording [4+2] heterocycloadducts of different stability. With chiral enamines a high asymmetric induction was observed in some cases. Some of the adducts were readily hydrolyzed to unsaturated gamma-nitroketones whereas others spontaneously rearranged to Diels-Alder-type carbocycloadducts.
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收藏
页码：5641 / 5644
页数：4
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