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

Literature Information

Publication Date 2008-09-12
DOI 10.1039/B810573A
Impact Factor 6.222
Authors

Nikolai Vinokurov, K. Michał Pietrusiewicz, Sławomir Frynas, Michael Wiebcke, Holger Butenschön


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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.

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