Issue 22, 2012
From the journal:

Chemical Communications

Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex†

Yasunori Yamamoto,*a   Tomohiko Shiraia  and  Norio Miyauraa  

* Corresponding authors

a Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, kita 13, nishi 8, Kita-ku, Sapporo 060-8628, Japan
E-mail: yasuyama@eng.hokudai.ac.jp
Fax: +81-11-706-6560
Tel: +81-11-706-6560

Abstract

The enantioselective synthesis of α-hydroxy esters by ruthenium-catalyzed 1,2-addition of arylboronic acids to tert-butyl glyoxylate is described. The use of RuCl2(PPh3)3 with (R,R)-Me-BIPAM gave optically active mandelic acids of up to 99% ee. Addition of a fluoride salt such as potassium fluoride (KF) or caesium fluoride (CsF) was effective for achieving high enantioselectivities.

Graphical abstract: Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex

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Article information

DOI
https://doi.org/10.1039/C2CC17339E
Article type
Communication
Submitted
24 Nov 2011
Accepted
13 Jan 2012
First published
17 Jan 2012

Chem. Commun., 2012,48, 2803-2805

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Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex

Y. Yamamoto, T. Shirai and N. Miyaura, Chem. Commun., 2012, 48, 2803 DOI: 10.1039/C2CC17339E

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