Issue 10, 2009
From the journal:

New Journal of Chemistry

Enantioselective catalysts for the Henry reaction: fine-tuning the catalytic components†

Edwin C. Constable,*a   Guoqi Zhang,a   Catherine E. Housecroft,*a   Markus Neuburger,a   Silvia Schaffner,a   Wolf-D. Woggona  and  Jennifer A. Zampesea  

* Corresponding authors

a Department of Chemistry, University of Basel, Spitalstrasse 51, CH 4056 Basel, Switzerland
E-mail: catherine.housecroft@unibas.ch
Fax: +41 61 267 1018
Tel: +41 61 267 1008

Abstract

Catalysts for the asymmetric Henry reaction involving 1,6-bis(3-ethoxy-2-hydroxyphenyl)-(3S,4S)-(−)-diphenyl-2,5-diazahexane (H22) and copper salts have been investigated. Conditions for the conversion of 4-nitrobenzaldehyde to 2-nitro-1-(4-nitrophenyl)ethanol by reaction with nitromethane have been optimized (5 mol% H22, 10 mol% CuI, THF, 295 K and 2 hours or 273 K and 12 hours) resulting in 99% yield and 90–92% ee. These catalytic conditions are effective for other aromatic aldehydes containing electron-withdrawing substituents, and for pyridine carbaldehydes; representative aliphatic aldehydes were converted to the respective β-hydroxynitro derivatives with good enantioselectivities, and in moderate yields. These catalytic conditions were found to be ineffective for simple aromatic aldehydes or those containing electron-releasing substituents.

Graphical abstract: Enantioselective catalysts for the Henry reaction: fine-tuning the catalytic components

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Article information

DOI
https://doi.org/10.1039/B9NJ00243J
Article type
Paper
Submitted
08 Jun 2009
Accepted
25 Jun 2009
First published
17 Aug 2009

New J. Chem., 2009,33, 2166-2173

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Enantioselective catalysts for the Henry reaction: fine-tuning the catalytic components

E. C. Constable, G. Zhang, C. E. Housecroft, M. Neuburger, S. Schaffner, Wolf-D. Woggon and J. A. Zampese, New J. Chem., 2009, 33, 2166 DOI: 10.1039/B9NJ00243J

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