Issue 91, 2013
From the journal:

Chemical Communications

Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst†

Isamu Shiina,*a   Keisuke Onoa  and  Takayoshi Nakaharaa  

* Corresponding authors

a Department of Applied Chemisty, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
E-mail: shiina@rs.kagu.tus.ac.jp
Fax: +81 3 3260 5609
Tel: +81 3 3260 4271

Abstract

A practical protocol is developed to directly provide chiral α-acyloxyphosphonates and α-hydroxyphosphonates from (±)-α-hydroxyphosphonates utilizing the transacylation process to generate the mixed anhydrides from acid components and pivalic anhydride in the presence of organocatalysts (s-value = 33–518).

Graphical abstract: Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst

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Article information

DOI
https://doi.org/10.1039/C3CC44293D
Article type
Communication
Submitted
07 Jun 2013
Accepted
21 Sep 2013
First published
23 Sep 2013

Chem. Commun., 2013,49, 10700-10702

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Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst

I. Shiina, K. Ono and T. Nakahara, Chem. Commun., 2013, 49, 10700 DOI: 10.1039/C3CC44293D

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