Issue 38, 2005
From the journal:

Chemical Communications

Organocatalytic asymmetric α-bromination of aldehydes and ketones†

Søren Bertelsen,a   Nis Halland,a   Stephan Bachmann,a   Mauro Marigo,a   Alan Brauntona  and  Karl Anker Jørgensen*a  

* Corresponding authors

a Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, Aarhus C, Denmark
E-mail: kaj@chem.au.dk
Fax: 45 8619 6199
Tel: 45 8942 3910

Abstract

The first organocatalytic enantioselective α-bromination of aldehydes and ketones is presented; a C2-symmetric diphenylpyrrolidine catalyst afforded the α-brominated aldehydes in good yields and up to 96% ee, while ketones were α-brominated by a C2-symmetric imidazolidine in up to 94% ee; furthermore, the organocatalytic enantioselective α-iodination of aldehydes is also demonstrated to proceed with up to 89% ee.

Graphical abstract: Organocatalytic asymmetric α-bromination of aldehydes and ketones

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Article information

DOI
https://doi.org/10.1039/B509366J
Article type
Communication
Submitted
01 Jul 2005
Accepted
26 Jul 2005
First published
30 Aug 2005

Chem. Commun., 2005, 4821-4823

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Organocatalytic asymmetric α-bromination of aldehydes and ketones

S. Bertelsen, N. Halland, S. Bachmann, M. Marigo, A. Braunton and K. A. Jørgensen, Chem. Commun., 2005, 4821 DOI: 10.1039/B509366J

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