18 research outputs found

    Stille Coupling of an Aziridinyl Stannatrane

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    An aziridinyl stannatrane <b>8</b> couples with aryl or alkenyl halides RX under modified Stille conditions to afford substituted aziridines. Efficient coupling at room temperature is possible in the best examples in the presence of (<sup><i>t</i></sup>Bu<sub>3</sub>P)<sub>2</sub>Pd and CuOP­(O)­Ph<sub>2</sub> (CuDPP)

    Asymmetric Synthesis of Cyclic <i>cis</i>-β-Amino Acid Derivatives Using Sulfinimines and Prochiral Weinreb Amide Enolates

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    Cyclic cis-β-amino Weinreb amides, valuable building blocks for the asymmetric synthesis of cyclic β-amino acids derivatives, are readily prepared via ring-closing metathesis of sulfinimine-derived N-sulfinyl β-amino diene Weinreb amides. These unsaturated cyclic cis-β-amino Weinreb amides are valuable building blocks for the asymmetric synthesis of cyclic β-amino acid derivatives

    Asymmetric Total Synthesis of (<i>S</i>)-(+)-Cocaine and the First Synthesis of Cocaine C-1 Analogs from <i>N</i>-Sulfinyl β-Amino Ester Ketals

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    Sulfinimine-derived α,β-unsaturated pyrrolidine nitrones, on heating with Al(O-t-Bu)3, undergo a highly stereoselective intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines, which are transformed in three-steps to give C-1 substituted cocaine analogs

    Asymmetric Total Synthesis of (<i>S</i>)-(+)-Cocaine and the First Synthesis of Cocaine C-1 Analogs from <i>N</i>-Sulfinyl β-Amino Ester Ketals

    No full text
    Sulfinimine-derived α,β-unsaturated pyrrolidine nitrones, on heating with Al(O-t-Bu)3, undergo a highly stereoselective intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines, which are transformed in three-steps to give C-1 substituted cocaine analogs

    Asymmetric Total Synthesis of (<i>S</i>)-(+)-Cocaine and the First Synthesis of Cocaine C-1 Analogs from <i>N</i>-Sulfinyl β-Amino Ester Ketals

    No full text
    Sulfinimine-derived α,β-unsaturated pyrrolidine nitrones, on heating with Al(O-t-Bu)3, undergo a highly stereoselective intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines, which are transformed in three-steps to give C-1 substituted cocaine analogs

    Asymmetric Synthesis of Substituted Tropinones Using the Intramolecular Mannich Cyclization Reaction and Acyclic <i>N</i>-Sulfinyl β-Amino Ketone Ketals

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    Sulfinimine-derived, enantiopure N-sulfinyl β-amino ketone ketals on hydrolysis give dehydropyrrolidine ketones that on treatment with (Boc)2O/DMAP afford substituted tropinones in good yield

    Asymmetric Synthesis of Substituted Tropinones Using the Intramolecular Mannich Cyclization Reaction and Acyclic <i>N</i>-Sulfinyl β-Amino Ketone Ketals

    No full text
    Sulfinimine-derived, enantiopure N-sulfinyl β-amino ketone ketals on hydrolysis give dehydropyrrolidine ketones that on treatment with (Boc)2O/DMAP afford substituted tropinones in good yield

    Asymmetric Total Synthesis of (<i>S</i>)-(+)-Cocaine and the First Synthesis of Cocaine C-1 Analogs from <i>N</i>-Sulfinyl β-Amino Ester Ketals

    No full text
    Sulfinimine-derived α,β-unsaturated pyrrolidine nitrones, on heating with Al(O-t-Bu)3, undergo a highly stereoselective intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines, which are transformed in three-steps to give C-1 substituted cocaine analogs

    Asymmetric Synthesis of Substituted Tropinones Using the Intramolecular Mannich Cyclization Reaction and Acyclic <i>N</i>-Sulfinyl β-Amino Ketone Ketals

    No full text
    Sulfinimine-derived, enantiopure N-sulfinyl β-amino ketone ketals on hydrolysis give dehydropyrrolidine ketones that on treatment with (Boc)2O/DMAP afford substituted tropinones in good yield

    Asymmetric Synthesis of Substituted Tropinones Using the Intramolecular Mannich Cyclization Reaction and Acyclic <i>N</i>-Sulfinyl β-Amino Ketone Ketals

    No full text
    Sulfinimine-derived, enantiopure N-sulfinyl β-amino ketone ketals on hydrolysis give dehydropyrrolidine ketones that on treatment with (Boc)2O/DMAP afford substituted tropinones in good yield
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