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A New Approach to the Asymmetric Reaction of the Chiron 5-L-Menthyloxy-2(5H)-furanones with Horner-Emmons Reagent
引用本文:李学强 王凤荣 何兰 陈庆华. A New Approach to the Asymmetric Reaction of the Chiron 5-L-Menthyloxy-2(5H)-furanones with Horner-Emmons Reagent[J]. 中国化学, 2003, 21(7): 805-810. DOI: 10.1002/cjoc.20030210719
作者姓名:李学强 王凤荣 何兰 陈庆华
作者单位:DepartmentofChemistry,BeijingNormalUniversity,Beijing100875,China
基金项目:Project supported by the National Natural Science Foundation of China(No.29672004).
摘    要:The asymmetric reaction of the chiron 2(5H )-furanones (4a-4c) with the Horner-Emmons reagents (5a-5b) has been investigated. The newly chirai organophosphorus derivatives 6 and 7 were obtained using the phosphoryl-stabilized carbanion as a building block in DMSO under mild conditions. Through the asymmetric introduction, the Horner-Emmons reagent could be transformed to a chiral building block to afford the novel functionalized phosphorus derivatives. The structures of the synthesized compounds 6 and 7 were identified on the basis of their elementary and spectroscopic data, such as IR,^1H NMR, ^13C NMR, MS and X-ray crystallography. These resuits provided a valuable approach to the synthesis of potentially interesting chirai organophosphorus derivatives and probing their biological activities.

关 键 词:不对称反应 手性5-L-孟氧基-2(5H)-呋喃酮 合成 生物学活性 X射线结晶分析 有机磷衍生物 Horner-Emmons试剂

A New Approach to the Asymmetric Reaction of the Chiron 5-L-MenthyIoxy-2(5H)-furanones with Horner-Emmons Reagent
LI,Xue-Qiang WANG,Feng-Kong HE,LanCHEN,Qing-Hua. A New Approach to the Asymmetric Reaction of the Chiron 5-L-MenthyIoxy-2(5H)-furanones with Horner-Emmons Reagent[J]. Chinese Journal of Chemistry, 2003, 21(7): 805-810. DOI: 10.1002/cjoc.20030210719
Authors:LI  Xue-Qiang WANG  Feng-Kong HE  LanCHEN  Qing-Hua
Affiliation:LI,Xue-Qiang WANG,Feng-Kong HE,LanCHEN,Qing-HuaDepartment of Chemistry,Beijing Normal University,Beijing 100875,China
Abstract:The asymmetric reaction of the chiron 2(5H)-furanones (4a-4c) with the Homer-Emmons reagents (5a-5b) has been investigated. The newly chiral organophosphorus derivatives 6 and 7 were obtained using the phosphoryl-stabilized carbanion as a building block in DMSO under mild conditions. Through the asymmetric introduction, the Horner-Emmons reagent could be transformed to a chiral building block to afford the novel functionalized phosphorus derivatives. The structures of the synthesized compounds 6 and 7 were identified on the basis of their elementary and spectroscopic data, such as IR, 1H NMR, 13C NMR, MS and X-ray crystallography. These results provided a valuable approach to the synthesis of potentially interesting chiral organophosphorus derivatives and probing their biological activities.
Keywords:chiron 2(5H)-furanones   asymmetric reaction  Horner-Emmons reagent   building block   chiral organophosphorus derivative   biological activity   X-ray crystallography
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