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Synthesis 2004(15): 2449-2458  
DOI: 10.1055/s-2004-831193
PAPER
© Georg Thieme Verlag Stuttgart · New York

A New Reaction System for Horner-Wadsworth-Emmons Olefination of Optically Active 4-Hydroxy-2-oxo-alkylphosphonates and 4-Hydroxy-1-chloro-2-oxo-alkylphosphonates with Aliphatic Aldehydes

Chengfu Xu, Chengye Yuan*
Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Lu, Shanghai, 200032, P. R. China
Fax: +86(21)64166128; e-Mail: yuancy@mail.sioc.ac.cn;
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Publication History

Received 14 May 2004
Publication Date:
23 August 2004 (online)

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Abstract

A new and convenient reaction system is described for the synthesis of chiral β′-hydroxy-α,β-unsatuarated ketones based on the Horner-Wadsworth-Emmons olefination of optically active 4-hydroxy-2-oxo-alkylphosphonates and 4-hydroxy-1-chloro-2-oxo-alkylphosphonates with aliphatic aldehydes.

Key words

2′-hydroxy-1,2-unsatuarated ketones - Horner-Wadsworth-Emmons reaction - 4-hydroxy-2-oxo-alkylphosphonates - 4-hydroxy-1-chloro-2-oxo- alkylphosphonates