Issue 42, 2008
From the journal:

Chemical Communications

Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: An efficient approach to novel P-stereogenic 1,2-diphosphine systems†

Nikolai Vinokurov,a   K. Michał Pietrusiewicz,*b   Sławomir Frynas,b   Michael Wiebckec  and  Holger Butenschön*a  

* Corresponding authors

a Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1B, Hannover, Germany
E-mail: holger.butenschoen@mbox.oci.uni-hannover.de
Fax: +49 (0)511 762-4616
Tel: +49 (0)511 762-4661

b Department of Organic Chemistry, Maria Curie-Skłodowska-University Lublin, ul. Gliniana 33, Lublin, Poland

c Institut für Anorganische Chemie, Leibniz Universität Hannover, Callinstraβe 9, Hannover, Germany

Abstract

The asymmetric 1,3-dipolar cycloaddition of the P-stereogenic dipolarophile (SP,SP)-6 to C,N-diphenylnitrone (7) led to previously unknown P-stereogenic isoxazolinyl diphosphine dioxides (RP,SP)-8 in enantio- and diastereomerically pure form; their stereospecific reduction with Ti(OiPr)4/PMHS proceeds in high yield with retention of configuration at the phosphorus atoms to give enantio- and diastereomerically pure diphosphines, which are conveniently purified via the corresponding diphosphine-diboranes.

Graphical abstract: Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: An efficient approach to novel P-stereogenic 1,2-diphosphine systems

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Article information

DOI
https://doi.org/10.1039/B810573A
Article type
Communication
Submitted
23 Jun 2008
Accepted
29 Jul 2008
First published
12 Sep 2008

Chem. Commun., 2008, 5408-5410

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Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: An efficient approach to novel P-stereogenic 1,2-diphosphine systems

N. Vinokurov, K. M. Pietrusiewicz, S. Frynas, M. Wiebcke and H. Butenschön, Chem. Commun., 2008, 5408 DOI: 10.1039/B810573A

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