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Gold-Catalyzed Direct Activation of Allylic Alcohols in the Stereoselective Synthesis of Functionalized 2-Vinyl-Morpholines

Authors

  • Dr. Marco Bandini,

    Corresponding author
    1. Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum - Università di Bologna via Selmi 2, 40126 Bologna (Italy), Fax: (+39) 51-2099456
    • Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum - Università di Bologna via Selmi 2, 40126 Bologna (Italy), Fax: (+39) 51-2099456
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  • Prof. Magda Monari,

    1. Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum - Università di Bologna via Selmi 2, 40126 Bologna (Italy), Fax: (+39) 51-2099456
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  • Alessandro Romaniello,

    1. Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum - Università di Bologna via Selmi 2, 40126 Bologna (Italy), Fax: (+39) 51-2099456
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  • Michele Tragni

    1. Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum - Università di Bologna via Selmi 2, 40126 Bologna (Italy), Fax: (+39) 51-2099456
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Abstract

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Alcohol versus alcohol: A highly stereocontrolled synthesis of substituted morpholines is realized by means of gold-catalyzed dehydrative allylic cyclization of diols (see scheme for one example; segphos = 5,5′-bis[di(3,5-di-tert-butyl-4-methyoxyphenyl)phosphine]-4,4′-bi-1,3-benzodioxole). The present methodology represents one of the few examples of enantioselective gold-catalyzed transformations involving unactivated alkenes.

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