Synthesis of optically active hydroxyphosphonates

✍ Scribed by Irina Guliaiko; Vitaly Nesterov; Sergei Sheiko; Oleg I. Kolodiazhnyi; Matthias Freytag; Peter G. Jones; Reinhard Schmutzler

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 235 KB
• Volume: 19
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20391

✦ Synopsis

Abstract

The reduction of dimenthyl ketophosphonates with sodium borohydride involves asymmetric induction at the α‐carbon atom, resulting in a small excess of the (R)‐enantiomer of the α‐hydroxyphosphonate formed. A higher ee purity was achieved if the reduction of chiral dimenthyl ketophosphonates was carried out by the chiral complex of NaBH~4~‐L‐proline, owing to the double asymmetric induction at the α‐carbon atom. The hydroxyphosphonates obtained were isolated in a diastereomerically pure state and were transformed to the optically active, free hydroxyalkylphosphonic acids. The (R)‐configuration of one of them was proved by X‐ray crystal structure analysis. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:133–139, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20391