Enantioselective Routes to Sulfoxides Based upon Carbon-for-Carbon Substitution Reactions on the Sulfinyl Group |
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| Authors: | Cosimo Cardellicchio Francesco Naso Maria Annunziata M. Capozzi |
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| Affiliation: | 1. Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti Organometallici (ICCOM), Sezione di Bari, Dipartimento di Chimica, Università di Bari , Italy;2. Dipartimento di Scienze Agro-ambientali, Chimica e Difesa Vegetale, Università degli Studi di Foggia , Foggia, Italy |
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| Abstract: | Abstract Grignard reagents were found to displace carbanionic leaving groups from suitable sulfinyl compounds. Because the process occurred with full inversion at the sulfinyl group, it was possible to set up an easy and straightforward route to chiral nonracemic sulfoxides. The starting compounds were easily produced, mainly by enantioselective oxidation of prochiral sulfides, and then the carbon-for-carbon displacement was effected with formation of a variety of new enantiopure sulfoxides. |
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| Keywords: | Carbanions Grignard reagents leaving groups sulfoxides |
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