Issue 20, 2014
From the journal:

Chemical Communications

Highly enantioselective synthesis of α-azido-β-hydroxy methyl ketones catalyzed by a cooperative proline–guanidinium salt system†

Ángel Martínez-Castañeda,a   Kinga Kędziora,a   Iván Lavandera,a   Humberto Rodríguez-Solla,a   Carmen Concellón*a  and  Vicente del Amo*a  

* Corresponding authors

a Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, C/Julián Clavería 8, Oviedo, Spain
E-mail: ccf@uniovi.es, vdelamo@uniovi.es

Abstract

The combined activity of (S)-proline and an achiral tetraphenylborate TBD-derived guanidinium salt permits the aldol reaction between azidoacetone and aromatic, or heteroaromatic aldehydes. The α-azido-β-hydroxy methyl ketones obtained as products can be isolated in good yield, with high diastereo- and enantioselectivity.

Graphical abstract: Highly enantioselective synthesis of α-azido-β-hydroxy methyl ketones catalyzed by a cooperative proline–guanidinium salt system

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Article information

DOI
https://doi.org/10.1039/C3CC49371G
Article type
Communication
Submitted
10 Dec 2013
Accepted
13 Jan 2014
First published
15 Jan 2014

Chem. Commun., 2014,50, 2598-2600

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Highly enantioselective synthesis of α-azido-β-hydroxy methyl ketones catalyzed by a cooperative proline–guanidinium salt system

Á. Martínez-Castañeda, K. Kędziora, I. Lavandera, H. Rodríguez-Solla, C. Concellón and V. del Amo, Chem. Commun., 2014, 50, 2598 DOI: 10.1039/C3CC49371G

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