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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页码：5641 / 5644

页数：4

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