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Simple Approach to the Highly Stereoselective Synthesis of trans-1,2-Cyclopropane Derivatives

Simple Approach to the Highly Stereoselective Synthesis of trans-1,2-Cyclopropane Derivatives
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摘要 In the presence of KF·2H2O, furoylmethyltriphenylarsonium bromide (1a) or thienoylmethyltriphenylarsonium bromide (1b) reacted with 2-[(un)substituted benzylidene]malononitrile (2) in chloroform at room temperature to give trans-3,3-dicyano-1-furoyl-2-[(un)substituted phenyl]cyclopropane (3a) or trans-3,3-dicyano-1-thienoyl-2- [(un)substituted phenyl]cyclopropane (3b) respectively in good yield with high stereoselectivity. The structures of product 3 were confirmed by IR, MS, 1^H NMR, 1^H-1^H COSY and microanalysis. The relative configuration of product 3 was determined by 1^H-1^H NOESY technique. The mechanism for the formation of product 3 was also proposed. In the presence of KF·2H2O, furoylmethyltriphenylarsonium bromide (1a) or thienoylmethyltriphenylarsonium bromide (1b) reacted with 2-[(un)substituted benzylidene]malononitrile (2) in chloroform at room temperature to give trans-3,3-dicyano-1-furoyl-2-[(un)substituted phenyl]cyclopropane (3a) or trans-3,3-dicyano-1-thienoyl-2- [(un)substituted phenyl]cyclopropane (3b) respectively in good yield with high stereoselectivity. The structures of product 3 were confirmed by IR, MS, 1^H NMR, 1^H-1^H COSY and microanalysis. The relative configuration of product 3 was determined by 1^H-1^H NOESY technique. The mechanism for the formation of product 3 was also proposed.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2007年第8期1187-1191,共5页 中国化学(英文版)
基金 Project supported by the National Natural Science Foundation of China (No. 20472047), the Natural Science Foundation of Shanghai (No. 04ZR14060) and the Education Commission of Shanghai Municipality (Nos. 05AX12 and B.99-0303-06-034).
关键词 stereoselective synthesis arsonium ylide cyclopropane derivative stereoselective synthesis, arsonium ylide, cyclopropane derivative
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