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Convenient synthesis of optically active α-hydroxyphosphinic acids

✍ Scribed by Juexiao Cai; Zhenghong Zhou; Guofeng Zhao; Chuchi Tang

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
93 KB
Volume
14
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

The reaction of O‐menthyl phenylphosphonite 1 with aromatic aldehydes in the presence of Me~3~SiCl provided the O‐menthyl α‐hydroxyphosphinates 2. Acidic hydrolysis of 2 gave the corresponding α‐hydroxyphosphinic acids 3. The (+)‐enantiomer of 3a and 3b, adduct of benzaldehyde and 4‐methylbenzaldehyde respectively, were obtained via multiple recrystallization. The absolute configuration of (+)‐3a was determined as S by X‐ray crystallography. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:312–315, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10150

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