Equilibration of the [2+2] Cycloaddition of Silyl Enol Ethers Catalyzed by Ethylaluminium Dichloride: Diastereoselectivity Switch in the Synthesis of Fused Cyclobutanes

被引：9

作者：

Hata, Kenji ^{[1
]}

Arichi, Norihito ^{[1
]}

Yamaoka, Yousuke ^{[1
]}

Yamada, Ken-ichi ^{[1
]}

Takemoto, Yoshiji ^{[1
]}

Takasu, Kiyosei ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 3卷 / 06期

关键词：

2+2] cycloadditions; cyclobutanes; ethylaluminium dichloride; silyl enol ethers; steroids; DERIVATIVES; CASCADE;

D O I：

10.1002/ajoc.201402042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The process by which the reaction between silyl enol ethers and acrylates reached equilibrium through an EtAlCl2-catalyzed [2+2] cycloaddition was characterized. The mechanism and substrate scope of the retro [2+2] cycloaddition were investigated. The trans or cis isomers can be selectively obtained by controlling the reaction temperature, although the substrate scope was found to be limited.

引用

页码：706 / 710

页数：5

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