Enantioselective Routes to Sulfoxides Based Upon the Use of Carbanionic Leaving Groups

Authors

  • Maria Annunziata M. Capozzi,

    1. Dipartimento di Scienze Agro-ambientali, Chimica e Difesa Vegetale, Facoltà di Agraria, Università degli Studi di Foggia, Via Napoli 25, 71100 Foggia, Italy, Fax: (internat.) + 39-081-740-211
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  • Cosimo Cardellicchio,

    1. Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti OrganoMetallici (ICCOM) Dipartimento di Chimica, Via Orabona 4, 70126 Bari, Italy, Fax: (internat.) + 39-080-544-2924
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  • Francesco Naso

    1. Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti OrganoMetallici (ICCOM) Dipartimento di Chimica, Via Orabona 4, 70126 Bari, Italy, Fax: (internat.) + 39-080-544-2924
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Abstract

Several carbanionic leaving groups can be easily displaced from the sulfinyl group by organometallic reagents. The reaction follows a highly stereoselective course of inversion of configuration. Provided that a ready route to the precursor sulfinyl compound is available (e.g. an enantioselective oxidation of the corresponding sulfide), the process can be transformed into an easy and versatile procedure for the stereoselective synthesis of sulfoxides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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