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Catalytic Asymmetric Mannich Reactions of Sulfonylacetates

Authors

  • Carlo Cassani,

    1. Department of Organic Chemistry “A. Mangini”, Faculty of Industrial Chemistry, University of Bologna, V. Risorgimento, 4, 40136 Bologna (Italy), Fax: (+39) 051-209-3654
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  • Luca Bernardi Dr.,

    1. Department of Organic Chemistry “A. Mangini”, Faculty of Industrial Chemistry, University of Bologna, V. Risorgimento, 4, 40136 Bologna (Italy), Fax: (+39) 051-209-3654
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  • Francesco Fini Dr.,

    1. Department of Organic Chemistry “A. Mangini”, Faculty of Industrial Chemistry, University of Bologna, V. Risorgimento, 4, 40136 Bologna (Italy), Fax: (+39) 051-209-3654
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  • Alfredo Ricci Prof.

    1. Department of Organic Chemistry “A. Mangini”, Faculty of Industrial Chemistry, University of Bologna, V. Risorgimento, 4, 40136 Bologna (Italy), Fax: (+39) 051-209-3654
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  • We acknowledge financial support from “Stereoselezione in Sintesi Organica Metodologie e Applicazioni” 2007. Financial support in the form of the Merck-ADP grant 2007 is also gratefully recognized. We thank Dr. M. Belén Cid for a useful suggestion, and E. Galletti for preliminary experiments.

Abstract

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Sulfon gegen Sulfon: Arylsulfonylacetate sind Syntheseäquivalente für eine Vielzahl an α-Carboxylatanionen. Durch Phasentransferkatalyse (PTC) gelangen ihre milde Deprotonierung und die katalytische asymmetrische Addition an hochreaktive, in situ aus α-Amidosulfonen erzeugte Imine (siehe Schema; Pg=Schutzgruppe). Die Nützlichkeit der Produkte in der Synthese wurde mit ihrer einfachen Überführung in eine Reihe von β-Aminosäurederivate gezeigt.

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