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Copper Phosphoramidite-Catalyzed Enantioselective Desymmetrization of meso-Cyclic Allylic Bisdiethyl Phosphates

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    Copper Phosphoramidite-Catalyzed Enantioselective Desymmetrization of meso-Cyclic Allylic Bisdiethyl Phosphates
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    Dipartimento di Scienze Chimiche, Fisiche e Matematiche, Università dell'Insubria, via Valleggio 11, I- 22100 Como, Italy, Dipartimento di Chimica Organica e Industriale, Centro di Eccellenza C.I.S.I., Università di Milano, via G. Venezian 21, I-20133 Milano, Italy, and Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
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    Organic Letters

    Cite this: Org. Lett. 2003, 5, 23, 4493–4496
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    https://doi.org/10.1021/ol035807l
    Published October 11, 2003
    Copyright © 2003 American Chemical Society
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    Abstract

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    A highly regio-, diastereo-, and enantioselective desymmetrization of five-, six-, and seven-membered meso-cyclic allylic bis-diethyl phosphates (2a, 2b, and 2c, respectively) was obtained with diethylzinc, using catalytic amounts of [Cu(OTf)]2·C6H6 and phosphoramidite ligands 5. Enantiomeric excesses of up to 87, 94, and >98% were obtained for the addition of diethylzinc to cyclopentene, cyclohexene, and cycloheptene bis-diethyl phosphates, respectively.

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     University of Insubria.

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     University of Milano.

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     University of Groningen.

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    Experimental details and characterization data, including 1H, 31P, and 13C NMR, IR, MS, and HRMS spectra and GC conditions. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: Org. Lett. 2003, 5, 23, 4493–4496
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol035807l
    Published October 11, 2003
    Copyright © 2003 American Chemical Society
    Request reuse permissions

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