Direct catalytic asymmetric aldol reaction of β-keto esters with formaldehyde promoted by a dinuclear Ni2-Schiff base complex

Shinsuke Mouri; Zhihua Chen; Shigeki Matsunaga; Masakatsu Shibasaki

doi:10.1039/B912380F

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Direct catalytic asymmetric aldol reaction of β-keto esters with formaldehyde promoted by a dinuclear Ni₂-Schiff base complex†‡

Shinsuke Mouri,^a Zhihua Chen,^a Shigeki Matsunaga*^a and Masakatsu Shibasaki*^a

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* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033, Japan
E-mail: mshibasa@mol.f.u-tokyo.ac.jp, smatsuna@mol.f.u-tokyo.ac.jp
Fax: +81-3-5684-5206
Tel: +81-3-5841-4830

Abstract

A homodinuclear Ni₂-Schiff base1 complex (0.1–1 mol%) promoted the direct catalytic asymmetric aldol reaction of β-keto esters with formaldehyde, giving hydroxymethylated adducts in 94–66% ee.

This article is part of the themed collection: Selective Catalysis for Organic Synthesis

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Supplementary files

General experimental information, spectral data of newcompounds, and copies of NMR spectral data PDF (7188K)

Article information

DOI: https://doi.org/10.1039/B912380F
Article type: Communication
Submitted: 23 6 2009
Accepted: 07 7 2009
First published: 24 7 2009

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Chem. Commun., 2009, 5138-5140

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Direct catalytic asymmetric aldol reaction of β-keto esters with formaldehyde promoted by a dinuclear Ni₂-Schiff base complex

S. Mouri, Z. Chen, S. Matsunaga and M. Shibasaki, Chem. Commun., 2009, 5138 DOI: 10.1039/B912380F

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Chemical Communications