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Organocatalytic Asymmetric Three-Component Cyclization of Cinnamaldehydes and Primary Amines with 1,3-Dicarbonyl Compounds: Straightforward Access to Enantiomerically Enriched Dihydropyridines

Authors

  • Jun Jiang,

    1. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences (CAS), Chengdu, 610041, China
    2. Graduate School of the Chinese Academy of Sciences, Beijing, China
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  • Jie Yu,

    1. Hefei National Laboratory for Physical Sciences at the Microscale
    2. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, Fax: (+86) 551-360-6266
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  • Xi-Xi Sun,

    1. Hefei National Laboratory for Physical Sciences at the Microscale
    2. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, Fax: (+86) 551-360-6266
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  • Qin-Quan Rao,

    1. Hefei National Laboratory for Physical Sciences at the Microscale
    2. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, Fax: (+86) 551-360-6266
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  • Liu-Zhu Gong Prof.

    1. Hefei National Laboratory for Physical Sciences at the Microscale
    2. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, Fax: (+86) 551-360-6266
    3. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences (CAS), Chengdu, 610041, China
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  • We are grateful for financial support from NSFC (20732006 and 20325211) and CAS.

Abstract

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Aller guten Dinge sind drei: Die Titelreaktion läuft unter milden Bedingungen in Gegenwart eines chiralen Phoshonsäure-Katalysators ab und liefert 4-arylsubstituierte 1,4-Dihydropyridine mit bis zu 98 % ee (siehe Schema). Die Produkte sind nützliche Substrate für die asymmetrische Synthese von Tetrahydropyridinen und Piperidinen, häufigen Teilstrukturen von Naturstoffen und Arzneimitteln. R1=Aryl; R2,R3=Alkyl.

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