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Highly Diastereo- and Enantioselective Synthesis of α-Alkyl Norstatine Derivatives: Catalytic Asymmetric Mannich Reactions of 5H-Oxazol-4-ones

Authors

  • Dr. Depeng Zhao,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, and Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
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    • These authors contributed equally to this work.

  • Linqing Wang,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, and Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
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    • These authors contributed equally to this work.

  • Dongxu Yang,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, and Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
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  • Yixin Zhang,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, and Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
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  • Prof. Dr. Rui Wang

    Corresponding author
    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, and Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
    • Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, and Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
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  • We are grateful for grants from the National Natural Science Foundation of China (nos. 90813012 and 20932003), the Key National S&T Program “Major New Drug Development” of the Ministry of Science and Technology (2012ZX09504001-003), and the Scholarship Award for Distinguished Doctoral Candidates of Lanzhou University.

Abstract

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Mannich für Fortgeschrittene: Die Titelreaktion ermöglicht die erste katalytische asymmetrische Synthese von syn-α-Alkylnorstatin-Derivaten. Mit dem Katalysatorsystem 1/Zn wurden mit einer Reihe von N-Diphenylphosphinoyl-geschützten Iminen und 5H-Oxazol-4-onen ausgezeichnete Enantio- und Diastereoselektivitäten erzielt. Das Diethylphosphoramidat 2 war entscheidend für gute Enantioselektivitäten in der vorgestellten Mannich-Reaktion.

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