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Diastereo- and Enantioselective Catalytic Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates with Alkyl-Substituted Aldehydes

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    Diastereo- and Enantioselective Catalytic Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates with Alkyl-Substituted Aldehydes
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    † Dipartimento Farmaceutico, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy
    ‡ Dipartimento di Chimica, Università degli Studi di Sassari, Via Vienna 2, I-07100 Sassari, Italy
    E-mail: [email protected]; [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2011, 76, 24, 10291–10298
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    https://doi.org/10.1021/jo201875a
    Published November 7, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    A reliable, catalytic asymmetric vinylogous Mukaiyama–Mannich reaction of pyrrole-based silyl dienolates is introduced that is particularly apt for alkyl- and α-alkoxyalkyl-substituted aldehydes. The reaction course is effectively orchestrated by the Hoveyda–Snapper amino acid-based chiral ligand/silver(I) catalyst combination to produce valuable vicinal diamino carbonyl compounds in high yields, with virtually complete γ-site- and anti-selectivity and significant catalyst-to-product chirality transfer. The utility of the Mannich products can be seen in the synthesis of an unprecedented perhydrofuro[3,2-b]pyrrolone product, an aza-analogue of naturally occurring (+)-goniofufurone.

    Copyright © 2011 American Chemical Society

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    General experimental information, full list of the optimization experiments, chiral HPLC traces, transition-state models, and copies of NMR spectra for new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2011, 76, 24, 10291–10298
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo201875a
    Published November 7, 2011
    Copyright © 2011 American Chemical Society
    Request reuse permissions

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