SmI2-promoted conjugate reduction of alpha,beta-unsaturated esters and ketones studied in comparison with Mukaiyama-Michael reaction of ketene silyl acetal

被引：30

作者：

Fujita, Y

Fukuzumi, S

Otera, J

机构：

[1] OSAKA UNIV,FAC ENGN,DEPT APPL CHEM,SUITA,OSAKA 565,JAPAN

[2] OKAYAMA UNIV SCI,DEPT APPL CHEM,OKAYAMA 700,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(97)00322-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

SmI2-promoted conjugate reduction of alpha,beta-unsaturated esters and ketones proceeds in a manner quite similar to Mukaiyama-Michael reaction of ketene silyl acetal. The more substituted esters are reduced more preferentially than the less substituted ones. The substrates with a 12 or 16 membered-ring structure undergo reduction smoothly. On the other hand, the 6-membered substrates completely fail to react under the same conditions. These results indicate generation of intermediate enolate radicals to be a key step for the conjugate reduction. (C) 1997 Elsevier Science Ltd.

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页码：2121 / 2124

页数：4

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