A New Family of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts

Authors

  • Marco Lombardo,

    Corresponding author
    1. Dipartimento di Chimica “G. Ciamician”, Università degli Studi di Bologna, via Selmi 2, 40126 Bologna, Italy, Fax: (+39)-051-2099456
    • Dipartimento di Chimica “G. Ciamician”, Università degli Studi di Bologna, via Selmi 2, 40126 Bologna, Italy, Fax: (+39)-051-2099456
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  • Elisa Montroni,

    1. Dipartimento di Chimica “G. Ciamician”, Università degli Studi di Bologna, via Selmi 2, 40126 Bologna, Italy, Fax: (+39)-051-2099456
    2. Consorzio Interuniversitario “C.I.N.M.P.I.S.”, via Orabona 4, 70125 Bari, Italy
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  • Arianna Quintavalla,

    1. Dipartimento di Chimica “G. Ciamician”, Università degli Studi di Bologna, via Selmi 2, 40126 Bologna, Italy, Fax: (+39)-051-2099456
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  • Claudio Trombini

    1. Dipartimento di Chimica “G. Ciamician”, Università degli Studi di Bologna, via Selmi 2, 40126 Bologna, Italy, Fax: (+39)-051-2099456
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Abstract

Simple chemical manipulations of trans-4-L-hydroxy proline allow the access to a new family of bicyclic silyl ether organocatalysts that display some remarkable features. Apart from being extremely stable to hydrolytic conditions and possessing excellent catalytic performances, the rigidity of the bicyclic structure imposes a synclinal endo disposition of the bulky substituents with respect to the pyrrolidine ring, opposed to the more stable synclinal exo conformations of Jørgensen–Hayashi catalysts.

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