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Vinokurov N, Pietrusiewicz KM, Frynas S, et al. Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: an efficient approach to novel P-stereogenic 1,2-diphosphine systems. Chem Commun (Camb). 2008;(42):5408-10doi: 10.1039/b810573a.
Vinokurov, N., Pietrusiewicz, K. M., Frynas, S., Wiebcke, M., & Butenschön, H. (2008). Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: an efficient approach to novel P-stereogenic 1,2-diphosphine systems. Chemical communications (Cambridge, England), (42), 5408-10. https://doi.org/10.1039/b810573a
Vinokurov, Nikolai, et al. "Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: an efficient approach to novel P-stereogenic 1,2-diphosphine systems." Chemical communications (Cambridge, England) vol. ,42 (2008): 5408-10. doi: https://doi.org/10.1039/b810573a
Vinokurov N, Pietrusiewicz KM, Frynas S, Wiebcke M, Butenschön H. Asymmetric 1,3-dipolar cycloaddition with a P-stereogenic dipolarophile: an efficient approach to novel P-stereogenic 1,2-diphosphine systems. Chem Commun (Camb). 2008 Nov 14;(42):5408-10. doi: 10.1039/b810573a. Epub 2008 Sep 12. PMID: 18985226.
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Chem Commun (Camb). 2008 Nov 14;(42):5408-10. doi: 10.1039/b810573a. Epub 2008 Sep 12.

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

Chemical communications (Cambridge, England)

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

Affiliations

  1. Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1B, Hannover, Germany.

PMID: 18985226 DOI: 10.1039/b810573a

Abstract

The asymmetric 1,3-dipolar cycloaddition of the P-stereogenic dipolarophile (S(p),S(p))-6 to C,N-diphenylnitrone (7) led to previously unknown P-stereogenic isoxazolinyl diphosphine dioxides (R(p),S(p))-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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