Stereoselective Synthesis of Polysubstituted Cyclopropanes from Poly(ethylene glycol) Supported Pyridinium Ylide

Chemical Research in Chinese Universities ›› 2011, Vol. 27 ›› Issue (6): 984-987.

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Stereoselective Synthesis of Polysubstituted Cyclopropanes from Poly(ethylene glycol) Supported Pyridinium Ylide

ZHAO Pan¹, LU Cui-fen¹, YANG Gui-chun¹, CHEN Zu-xing^1*, DONG Nian-guo² and SHI Jia-wei²

1. Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, College of Chemistry and Chemical Engineering, Hubei University, Wuhan 430000, P. R. China;
2.Department of Cardiovarscular Surgery, Union Hospital, Tongji Medical College, Huazhong Science and Technology University, Wuhan 430072, P. R. China

Received:2010-12-01 Revised:2011-06-14 Online:2011-11-25 Published:2011-11-07
Contact: CHEN Zu-xing E-mail:chzux@hubu.edu.cn
Supported by:
Supported by the National High Technology Research and Development Program of China(No.2009AA03Z420) and the Natural Science Foundation of Hubei Province of China(Nos.2007ABA031, 2008CDA078).

Abstract

Abstract: Polysubstituted cyclopropanes were efficiently prepared with poly(ethylene glycol)(PEG) as soluble support. The reaction of PEG-supported pyridinium ylide with arylidenemalononitrile(R=CN) or ethyl arylidenecyanoacetate(R=COOEt) in the presence of triethylamine(TEA) afforded PEG-supported cyclopropanecarboxylates, which were cleaved by 1% KCN/EtOH to obtain polysubstituted cyclopropanes with exclusive trans-selectivity and good yields.

Key words: Poly(ethylene glycol), Pyridinium ylide, Synthesis, Cyclopropane

ZHAO Pan, LU Cui-fen, YANG Gui-chun, CHEN Zu-xing*, DONG Nian-guo and SHI Jia-wei. Stereoselective Synthesis of Polysubstituted Cyclopropanes from Poly(ethylene glycol) Supported Pyridinium Ylide[J]. Chemical Research in Chinese Universities, 2011, 27(6): 984-987.

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Stereoselective Synthesis of Polysubstituted Cyclopropanes from Poly(ethylene glycol) Supported Pyridinium Ylide

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