Issue 21, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Diastereoselective Lewis acid mediated hydrophosphonylation of heterocyclic imines: a stereoselective approach towards α-amino phosphonates

Imre Schlemminger,a   Andreas Willecke,a   Wolfgang Maison,a   Rainer Koch,a   Arne Lützena  and  Jürgen Martens*a  

* Corresponding authors

a Department of Chemistry, University of Oldenburg, P. O. Box 2503, 26111 Oldenburg, Germany
E-mail: juergen.martens@uni-oldenburg.de

Abstract

The synthesis of new chiral α-amino phosphonates by the Lewis acid mediated addition of bisesters of phosphonic acid to 3-thiazolines (2,5-dihydro-1,3-thiazoles), is described. The diastereoselectivity of the reaction using chiral reactants was systematically investigated. The chiral BINOL-phosphonate 1 was found to be a highly stereoselective phosphonylating agent towards 3-thiazolines. Structural aspects of the resulting thiazolidinylphosphonates were studied by NMR and X-ray analyses. The role of the Lewis acid as a spatial mediator is discussed and a quantum chemical description of the Lewis acid mediated hydrophosphonylation presented.

Graphical abstract: Diastereoselective Lewis acid mediated hydrophosphonylation of heterocyclic imines: a stereoselective approach towards α-amino phosphonates

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Article information

DOI
https://doi.org/10.1039/B101501J
Article type
Paper
Submitted
14 Feb 2001
Accepted
29 Aug 2001
First published
09 Oct 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2804-2816

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Diastereoselective Lewis acid mediated hydrophosphonylation of heterocyclic imines: a stereoselective approach towards α-amino phosphonates

I. Schlemminger, A. Willecke, W. Maison, R. Koch, A. Lützen and J. Martens, J. Chem. Soc., Perkin Trans. 1, 2001, 2804 DOI: 10.1039/B101501J

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