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Organocatalytic Asymmetric Hydrophosphination of α,β-Unsaturated Aldehydes

Authors

  • Armando Carlone,

    1. Department of Organic Chemistry “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento, 4, 40136 Bologna, Italy, Fax: (+39) 051-209-3654
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  • Giuseppe Bartoli Prof.,

    1. Department of Organic Chemistry “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento, 4, 40136 Bologna, Italy, Fax: (+39) 051-209-3654
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  • Marcella Bosco Prof.,

    1. Department of Organic Chemistry “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento, 4, 40136 Bologna, Italy, Fax: (+39) 051-209-3654
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  • Letizia Sambri Dr.,

    1. Department of Organic Chemistry “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. Department of Organic Chemistry “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 the MIUR, Rome, and the FIRB National Project “Progettazione, preparazione e valutazione farmacologica di nuove molecole organiche quali potenziali farmaci innovativi”.

Abstract

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Von N zu P: Eine hoch chemo- und enantioselektive konjugierte Addition von Diphenylphosphan an α,β-ungesättigte Aldehyde in Gegenwart eines chiralen sekundären Amins C liefert direkt chirale β-Phosphinoaldehyd-Intermediate (siehe Schema, TMS=Trimethylsilyl). Die Nützlichkeit dieser Strategie wird mit einer zweistufigen Eintopfsynthese von hoch enantiomerenangereicherten 3-Aminophosphanen belegt.

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