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A New Approach to the Asymmetric Reaction of the Chiron 5-L-Menthyloxy-2(5H)-furanones with Horner-Emmons Reagent

✍ Scribed by Xue-Qiang Li; Feng-Rong Wang; Lan He; Qing-Hua Chen

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 536 KB
Volume: 21
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.20030210719

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✦ Synopsis

Abstract

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.

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