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Enantioselective Synthesis of α-Alkyl-β-ketoesters: Asymmetric Roskamp Reaction Catalyzed by an Oxazaborolidinium Ion

Authors

  • Lizhu Gao,

    1. Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-Dong, Jangan-gu, Suwon, Gyeoneggi, 440-746 (Korea)
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  • Byung Chul Kang,

    1. Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-Dong, Jangan-gu, Suwon, Gyeoneggi, 440-746 (Korea)
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  • Prof. Dr. Geum-Sook Hwang,

    Corresponding author
    1. Korea Basic Science Institute and Graduate School of Analytical Science and Technology, Chungnam National University, Seoul, 136-713 (Korea)
    • Korea Basic Science Institute and Graduate School of Analytical Science and Technology, Chungnam National University, Seoul, 136-713 (Korea)
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  • Prof. Dr. Do Hyun Ryu

    Corresponding author
    1. Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-Dong, Jangan-gu, Suwon, Gyeoneggi, 440-746 (Korea)
    • Department of Chemistry, Sungkyunkwan University, 300 Cheoncheon-Dong, Jangan-gu, Suwon, Gyeoneggi, 440-746 (Korea)
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  • This work was supported by grants NRF-2011-0031392 (Priority Research Centers Program), NRF-2011-0029186 (Midcareer Researcher Program) and the Korea Basic Science Institute (T32409).

Abstract

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Breaking kamp: A catalytic route toward chiral α-alkyl-β-ketoesters using the title reaction of α-alkyl diazoester with aldehydes has been developed (see scheme). The reaction proceeds with high to excellent enantioselectivities and this methodology was applied to a concise two-step synthesis of the natural pheromone sitophilate.

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