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

高等学校化学研究 ›› 2011, Vol. 27 ›› Issue (6): 984-987.

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

收稿日期:2010-12-01 修回日期:2011-06-14 出版日期:2011-11-25 发布日期:2011-11-07
通讯作者: CHEN Zu-xing E-mail:chzux@hubu.edu.cn
基金资助:
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).

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).

摘要/Abstract

摘要： 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.

关键词: Poly(ethylene glycol), Pyridinium ylide, Synthesis, Cyclopropane

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-we. Stereoselective Synthesis of Polysubstituted Cyclopropanes from Poly(ethylene glycol) Supported Pyridinium Ylide[J]. 高等学校化学研究, 2011, 27(6): 984-987.

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

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

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