Issue 11, 2006
From the journal:

Organic & Biomolecular Chemistry

Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases

Peter Dinéra  and  Mohamed Amedjkouh*a  

* Corresponding authors

a Organic Chemistry, Department of Chemistry, Göteborg University, Göteborg, Sweden
E-mail: mamou@chem.gu.se
Fax: +46 31 772 3840

Abstract

Chiral α-aminophosphonates have been synthesized and their performance was evaluated as organocatalysts in the direct asymmetric aldol reaction. High enantioselectivities (up to 99% ee) were achieved for a range of substituted cyclohexanones and benzaldehydes. Several organic bases, such as DBU, DBN, and TMG, were used together with the α-aminophosphonates in the aldol reactions and were found to favor syn-selectivity.

Graphical abstract: Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases

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Article information

DOI
https://doi.org/10.1039/B605091C
Article type
Communication
Submitted
04 Oct 2005
Accepted
18 Apr 2006
First published
09 May 2006

Org. Biomol. Chem., 2006,4, 2091-2096

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Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases

P. Dinér and M. Amedjkouh, Org. Biomol. Chem., 2006, 4, 2091 DOI: 10.1039/B605091C

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