Issue 10, 2009
From the journal:

Organic & Biomolecular Chemistry

Highly diastereo- and enantioselective organocatalytic addition of acetone to β-substituted α-ketoesters via dynamic kinetic resolution†

Jin Yang,a   Ting Wang,a   Zhenhua Ding,a   Zongxuan Shena  and  Yawen Zhang*a  

* Corresponding authors

a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Suzhou, China
E-mail: zhangyw@suda.edu.cn
Fax: +86 512 65880305
Tel: +86 512 65880340

Abstract

L-Proline catalyzes the aldol addition reaction of acetone to β-substituted α-ketoesters with dynamic kinetic resolution, providing the desired adduct in good yield with excellent diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to 98% ee). The absolute configuration of the chiral adduct was assigned by single-crystal X-ray diffraction analysis. A tentative explanation of the stereochemical outcome is proposed.

Graphical abstract: Highly diastereo- and enantioselective organocatalytic addition of acetone to β-substituted α-ketoesters via dynamic kinetic resolution

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Article information

DOI
https://doi.org/10.1039/B822127H
Article type
Paper
Submitted
09 Dec 2008
Accepted
17 Mar 2009
First published
16 Apr 2009

Org. Biomol. Chem., 2009,7, 2208-2213

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Highly diastereo- and enantioselective organocatalytic addition of acetone to β-substituted α-ketoesters via dynamic kinetic resolution

J. Yang, T. Wang, Z. Ding, Z. Shen and Y. Zhang, Org. Biomol. Chem., 2009, 7, 2208 DOI: 10.1039/B822127H

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