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

Imre Schlemminger; Andreas Willecke; Wolfgang Maison; Rainer Koch; Arne Lützen; Jürgen Martens

doi:10.1039/B101501J

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Journal of the Chemical Society, Perkin Transactions 1

Issue 21, 2001

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

Imre Schlemminger , Andreas Willecke , Wolfgang Maison , Rainer Koch , Arne Lützen and Jürgen Martens

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

DOI: 10.1039/B101501J
Received 14 Feb 2001, Accepted 29 Aug 2001
First published on the web 09 Oct 2001

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Abstract
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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.

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Imre Schlemminger
Andreas Willecke
Wolfgang Maison
Rainer Koch
Arne Lützen
Jürgen Martens

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Journal of the Chemical Society, Perkin Transactions 1

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

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