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A New Approach to the Asymmetric Reaction of the Chiron 5‐ L ‐Menthyloxy‐2(5 H )‐furanones with Horner‐Emmons Reagent
Author(s) -
Li XueQiang,
Wang FengRong,
He Lan,
Chen QingHua
Publication year - 2003
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20030210719
Subject(s) - chemistry , reagent , carbanion , block (permutation group theory) , medicinal chemistry , phosphorus , combinatorial chemistry , organic chemistry , stereochemistry , geometry , mathematics
The asymmetric reaction of the chiron 2(5 H )‐furanones (4a–4c) with the Horner‐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, 1 H NMR, 13 C 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.