Stereoselective cyclopropanation of ¦Á-bromochalcone with diethyl malonate promoted by K₂CO₃

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• 作者：Yongxian Sun ; Gaosheng Yang ; ^{gshyang@mail.ahnu.edu.cn} ; Yue Shen ; Zan Hua ; Zhuo Chai ; ^{chaizhuo@live.cn}
• 关键词：Stereoselective cyclopropanation ; Cyclopropane-1 ; 1-dicarboxylates ; ¦Á-Bromochalcone ; Malonate ; Michael addition
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：1 April, 2013
• 年：2013
• 卷：69
• 期：13
• 页码：2733-2739
• 全文大小：397 K

文摘

A new Michael-initiated cyclopropanation reaction using ¦Á-bromochalcones as Michael acceptor was developed. Compared to previous works using arylidenemalonates as Michael acceptor, this novel protocol could improve the synthesis of trans-isomers of diethyl 2-benzoyl-3-phenyl-cyclopropane-1,1-dicarboxylates. More importantly, this method also provided the first access to the cis-isomers of these densely substituted cyclopropanes with the Michael-initiated ring closure (MIRC) strategy, albeit with a poor diastereoselectivity.