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Design of the Chiral Environment for Asymmetric Acid-Base Catalysis

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Designed Molecular Space in Material Science and Catalysis

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Abstract

Asymmetric catalysis is one of the most powerful methodologies for engineering chiral molecules. But, despite significant advances, there have been few systematic studies aiming to explore and expand the available “catalytic asymmetric space.” In general, optimization of the selectivity (enantio-, diastereo-, regio-, and chemoselectivity) of asymmetric catalysis relies on trial-and-error screening using the inherent stereochemistry embedded in “privileged” chiral templates. This review describes our nascent efforts to broaden the conceptual basis of catalyst design, focusing on the development of two different classes of asymmetric catalysts including (1) conformationally flexible guanidine/bisthiourea organocatalysts and (2) centrochiral transition-metal catalysts. We will also discuss physical-organic chemical methodologies available to explore the interplay of structure and selectivity in asymmetric acid-base catalysis.

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Authors and Affiliations

  1. Synthetic Organic Chemistry lab, RIKEN Cluster for Pioneering Research, Saitama, Japan

    Yoshihiro Sohtome & Mikiko Sodeoka

  2. Catalysis and Integrated Research Group, RIKEN Center for Sustainable Resource Science, Saitama, Japan

    Yoshihiro Sohtome & Mikiko Sodeoka

  3. Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, Tokyo, Japan

    Kazuo Nagasawa

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  1. Yoshihiro Sohtome
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  2. Kazuo Nagasawa
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Correspondence to Yoshihiro Sohtome .

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  1. Department of Environmental Science Graduate School of Fisheries and Environmental Sciences, Nagasaki University, Nagasaki, Japan

    Seiji Shirakawa

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Sohtome, Y., Nagasawa, K., Sodeoka, M. (2018). Design of the Chiral Environment for Asymmetric Acid-Base Catalysis. In: Shirakawa, S. (eds) Designed Molecular Space in Material Science and Catalysis. Springer, Singapore. https://doi.org/10.1007/978-981-13-1256-4_5

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