Issue 25, 2012
From the journal:

Organic & Biomolecular Chemistry

Asymmetric Michael addition of boronic acids to a γ-hydroxy-α,β-unsaturated aldehyde catalyzed by resin-supported peptide†‡

Kengo Akagawa,a   Masahide Sugiyamaa  and  Kazuaki Kudo*a  

* Corresponding authors

a Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan
E-mail: kkudo@iis.u-tokyo.ac.jp
Fax: +81 3 5452 6357
Tel: +81 3 5452 6359

Abstract

A resin-supported peptide catalyst effective for the asymmetric Michael addition of boronic acids to (E)-4-hydroxybut-2-enal was developed. From a spectral study, it was revealed that the optimum peptide consisted of both a β-turn and helix. Such a combination of secondary structures was essential for achieving a high catalytic ability.

Graphical abstract: Asymmetric Michael addition of boronic acids to a γ-hydroxy-α,β-unsaturated aldehyde catalyzed by resin-supported peptide

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Article information

DOI
https://doi.org/10.1039/C2OB25431J
Article type
Communication
Submitted
28 Feb 2012
Accepted
21 May 2012
First published
24 May 2012

Org. Biomol. Chem., 2012,10, 4839-4843

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Asymmetric Michael addition of boronic acids to a γ-hydroxy-α,β-unsaturated aldehyde catalyzed by resin-supported peptide

K. Akagawa, M. Sugiyama and K. Kudo, Org. Biomol. Chem., 2012, 10, 4839 DOI: 10.1039/C2OB25431J

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