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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 19
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Original Articles

Facile, Highly Stereoselective Synthesis of Cyclopropyl Benzoimidazoles via Cyclopropanation of Olefin with Arsonium Ylides

Weiqi Tong Department of Chemistry, Shanghai University, Shanghai, China
,
Changqing Wang Department of Chemistry, Shanghai University, Shanghai, China
,
Wenwen Zhao Department of Chemistry, Shanghai University, Shanghai, China
,
Jie Chen Department of Chemistry, Shanghai University, Shanghai, China
,
Xiaoyu Wu Department of Chemistry, Shanghai University, Shanghai, China
,
Min Zhang Department of Chemistry, Shanghai University, Shanghai, China
,
Hongmei Deng Instrumental Analysis and Research Center, Shanghai University, Shanghai, China
,
Min Shao Instrumental Analysis and Research Center, Shanghai University, Shanghai, China
,
Zhongjiao Ren Department of Chemistry, Shanghai University, Shanghai, China
&
Weiguo Cao Department of Chemistry, Shanghai University, Shanghai, China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai, ChinaCorrespondence[email protected]
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Pages 3471-3481 | Received 23 Oct 2008, Published online: 04 Sep 2009
 
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Abstract

A facile and highly stereoselective methodology for the preparation of highly functionalized trans-1,2-cyclopropanes containing benzoimidazolyl, cyano, aryl, and carbonyl groups 3 is described. Arsonium bromides 2 reacted with electron-deficient olefins 1 in the presence of KF·2H2O to provide 3 exclusively with high stereoselectivity in moderate to good yields.

ACKNOWLEDGMENTS

Financial support from the National Natural Science Foundation of China (No. 20482088), the Leading Academic Discipline Project, and the Foundation of Education Commission of Shanghai Municipality (Grant Nos. 08ZZ44 and J50102) is acknowledged.

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