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
收藏
页码：706 / 710
页数：5
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