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Site-Selective Conjugate Addition Through Catalytic Generation of Ion-Pairing Intermediates

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Site-Selective Catalysis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 372))

Abstract

Site-selectivity in conjugate addition reactions is tightly associated with the principle of vinylogy. Various vinylogous nucleophiles and electrophiles have been applied to stereoselective conjugate additions directed by chiral small-molecule catalysts. This chapter focuses on the systems that control site- and stereoselectivity via chiral ion-pairing intermediates under organocatalytic conditions and describes individual vinylogous substrates in a separate section. Although site-selectivity originates largely from the intrinsic stereoelectronic nature of individual substrates, catalyst-controlled site-selectivity can be attained in certain cases.

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Author information

Authors and Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo cho, Chikusa ku, Nagoya, Aichi, 464-8602, JAPAN

    Daisuke Uraguchi

  2. Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, and CREST, Japan Science and Technology Agency (JST), Furo cho, Chikusa ku, Nagoya, Aichi, 464-8602, JAPAN

    Takashi Ooi

Authors
  1. Daisuke Uraguchi
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  2. Takashi Ooi
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Correspondence to Takashi Ooi .

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Editors and Affiliations

  1. Institute for Chemical Research Kyoto University, Kyoto, Japan

    Takeo Kawabata

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© 2015 Springer International Publishing Switzerland

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Uraguchi, D., Ooi, T. (2015). Site-Selective Conjugate Addition Through Catalytic Generation of Ion-Pairing Intermediates. In: Kawabata, T. (eds) Site-Selective Catalysis. Topics in Current Chemistry, vol 372. Springer, Cham. https://doi.org/10.1007/128_2015_655

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