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Stereoselective Synthesis of Multiple Stereocenters by Using a Double Aldol Reaction

Authors

  • Yasushi Shimoda,

    1. Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973 (Japan)
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  • Tatsunori Kubo,

    1. Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973 (Japan)
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  • Prof. Dr. Masaharu Sugiura,

    1. Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973 (Japan)
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  • Prof. Dr. Shunsuke Kotani,

    Corresponding author
    1. Priority Organization for Innovation and Excellence, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973 (Japan)
    • Priority Organization for Innovation and Excellence, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973 (Japan)
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  • Prof. Dr. Makoto Nakajima

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973 (Japan)
    • Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Chuo-ku, Kumamoto 862-0973 (Japan)
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  • This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

Abstract

original image

In einer Stufe führt die Titelreaktion eines Alkylmethylketons mit zwei Aldehyden mit guten Ausbeuten zu 1,5-Dihydroxy-3-pentanon-Derivaten. Durch den Einsatz des chiralen Lewis-Base-Katalysators (S)-Binapo werden die Chiralitätszentren der Produkte hoch diastereo- und enantioselektiv aufgebaut.

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