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One-Step Stereocontrol of Three Contiguous Stereogenic Centers in Acyclic Systems: The Tuning Effect of an Additive in a Tandem Asymmetric Michael Addition and Meerwein–Ponndorf–Verley Reduction

Authors

  • Kiyoharu Nishide Prof. Dr.,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Minoru Ozeki,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Hideaki Kunishige,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Yukihiro Shigeta,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Pranab K. Patra Dr.,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Yuri Hagimoto Dr.,

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • Manabu Node Prof. Dr.

    1. Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775
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  • We are grateful to the Ministry of Education, Culture, Sports, Science, and Technology of Japan for partial support of this research [Grant-in-Aid for Scientific Research (B) (13470474)]. P.K.P. acknowledges the JSPS for a postdoctoral fellowship.

Abstract

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Bei Additions-Reduktions-Dominoreaktionen entstehen mit hoher Diastereoselektivität drei benachbarte Stereozentren. Das chirale Thiol 1 reagiert in einer Michael-Addition mit acyclischen α,β-disubstitutierten α,β-ungesättigten Ketonen 2 (siehe Schema). Bei der Untersuchung von Additiven stellte sich heraus, dass die Verbindungen 3 geeignete Vorstufen für die 1,3-Hydroxythiole 4 sind. R1=Aryl, R2=Alkyl, R3=Alkyl oder Phenyl.

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