From the Feist–Bénary Reaction to Organocatalytic Domino Michael–Alkylation Reactions: Asymmetric Synthesis of 3(2 H)-Furanones

Authors

  • Xiaowei Dou,

    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
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  • Xiaoyu Han,

    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
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  • Prof. Dr. Yixin Lu

    Corresponding author
    1. Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
    • Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6779-1691
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Abstract

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It all adds up! A modified Feist–Bénary reaction employing a domino Michael–alkylation sequence was designed for the enantioselective synthesis of 3(2 H)-furanones. L-Threonine-derived tertiary amine/thiourea catalysts were prepared for the first time; such catalysts promoted the designed domino Michael–alkylation reactions in a highly enantioselective manner (see scheme).

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