Enantioselective organocatalytic Michael reactions using chiral (R,R)-1,2-diphenylethylenediamine-derived thioureas

Jae Ho Shim, Min Ji Lee, Min Ho Lee, Byeong Seon Kim, Deok Chan Ha

    Research output: Contribution to journalArticlepeer-review

    8 Citations (Scopus)

    Abstract

    Although the Michael addition is a very well-known and widely applied reaction, cost-effective, metal-free, and readily prepared organic catalysts remain rare. A chiral, bifunctional, (R,R)-1,2-diphenylethylenediamine-derived thiourea organic catalyst was developed and applied to asymmetric Michael additions of nitroalkenes under neutral conditions. Generally, fluorine-substituted thiourea catalysts exhibited high chemical yields and enantioselectivities under neutral conditions. The mild reactions were tolerant of many functional groups and afforded good-to-excellent yields, as well as high diastereo- and enantioselectivities for the Michael adducts. The utility of the transformation was demonstrated by the synthesis of a bioactive compound, (R)-Phenibut.

    Original languageEnglish
    Pages (from-to)31808-31814
    Number of pages7
    JournalRSC Advances
    Volume10
    Issue number53
    DOIs
    Publication statusPublished - 2020 Aug 27

    Bibliographical note

    Funding Information:
    We are grateful for nancial support by Dr K. H. Kim. We gratefully acknowledge the support from National Research Foundation of Korea (NRF-2019R1814112), (NRF-2020R1C1C1-013785). We thank Dr Yeonsun Hong for providing assistance.

    Publisher Copyright:
    © The Royal Society of Chemistry 2020.

    ASJC Scopus subject areas

    • General Chemistry
    • General Chemical Engineering

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