FACILE REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN EPOXY-ALLYLIC STANNANE CYCLIZATIONS

被引：9

作者：

YOSHITAKE, M

YAMAMOTO, M

KOHMOTO, S

YAMADA, K

机构：

[1] CHIBA UNIV,FAC ENGN,DEPT MAT SCI,1-33 YAYOI CHO,CHIBA 260,JAPAN

[2] CHIBA UNIV,GRAD SCH SCI & TECHNOL,CHIBA 260,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 09期

关键词：

D O I：

10.1039/p19910002161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid and butyllithium promoted cyclisations of epoxy-allylic stannanes have been studied. The regio-and stereo-chemistry of the cyclisations are described. The stereoelectronically favoured 5-and 6-membered ring formations have been explained by either the electronic nature of, or the steric hindrance induced by, the epoxide moiety of the substrates depending on whether the reaction was promoted by a Lewis acid or butyllithium, respectively. The different stereoselectivities observed are brought about by the mode of reaction. The contrasting results for the 5-membered ring formations are particularly remarkable.

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页码：2161 / 2167

页数：7

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