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Organocatalytic Asymmetric α-Selenenylation of Aldehydes

Authors

  • Marcello Tiecco Prof.,

    1. Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy, Fax: (+39) 075-585-5116
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  • Armando Carlone,

    1. Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento, 4, 40136 Bologna, Italy, Fax: (+39) 051-209-3654
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  • Silvia Sternativo Dr.,

    1. Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy, Fax: (+39) 075-585-5116
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  • Francesca Marini Prof.,

    1. Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy, Fax: (+39) 075-585-5116
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  • Giuseppe Bartoli Prof.,

    1. Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento, 4, 40136 Bologna, Italy, Fax: (+39) 051-209-3654
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  • Paolo Melchiorre Dr.

    1. Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento, 4, 40136 Bologna, Italy, Fax: (+39) 051-209-3654
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  • This work was carried out in the framework of the National Project “Stereoselezione in Sintesi Organica” supported by MIUR, Rome. Financial support from the Consorzio CINMPIS, Bari, is also gratefully acknowledged.

Abstract

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Getting round the (periodic) table: The enamine activation concept has been extended to the asymmetric addition of selenium-based compounds to aldehydes in an organocatalytic transformation that provides high reaction efficiency and stereocontrol (ee values ranging from 95 to 99 %) with readily available chiral secondary amines. The chiral α-seleno aldehydes thus formed can be used as versatile intermediates .

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