Convenient synthesis of optically active α‐hydroxyphosphinic acids

Abstract

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