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The Direct Asymmetric Vinylogous Aldol Reaction of Furanones with α-Ketoesters: Access to Chiral γ-Butenolides and Glycerol Derivatives

Authors

  • Jie Luo,

    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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  • Haifei Wang,

    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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  • Xiao 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. Li-Wen Xu,

    1. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University (P R China)
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  • Jacek Kwiatkowski,

    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. Kuo-Wei Huang,

    1. KAUST Catalysis Center and Division of Chemical and Life Sciences and Engineering, King Abdullah University of Science and Technology (Kingdom of Saudi Arabia)
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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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  • We thank the National University of Singapore and the Ministry of Education (MOE) of Singapore (R-143-000-362-112) for generous financial support.

Abstract

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Twice as good: The title reaction using the tryptophan-derived bifunctional organic catalyst 1 has been developed. The reported method led to the synthesis of chiral γ-substituted butenolides in excellent yields, with high diastereo- and enantioselectivities. Facile synthesis of chiral glycerol derivatives containing a tertiary hydroxy group has also been demonstrated.

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