Chiral primary amino alcohol organobase catalysts for the asymmetric Diels-Alder reactions of anthrones with maleimides

Jun Kumagai, Teppei Otsuki, U. V. Subba Reddy, Yoshihito Kohari, Chigusa Seki, Koji Uwai, Yuko Okuyama, Eunsang Kwon, Michio Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

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16 Citations (Scopus)

Abstract

Simple chiral triethylsilyl-amino alcohol organocatalysts containing a bulky triethylsilyl group on the oxygen atom at the γ-position were designed and synthesized as new organocatalysts for enantioselective Diels-Alder reactions of anthrones with maleimides to produce chiral hydroanthracene Diels-Alder adducts in up to 99% yield and with up to 94% ee.

Original languageEnglish
Pages (from-to)1423-1429
Number of pages7
JournalTetrahedron Asymmetry
Volume26
Issue number24
DOIs
Publication statusPublished - 2015 Dec 31

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Kumagai, J., Otsuki, T., Subba Reddy, U. V., Kohari, Y., Seki, C., Uwai, K., Okuyama, Y., Kwon, E., Tokiwa, M., Takeshita, M., & Nakano, H. (2015). Chiral primary amino alcohol organobase catalysts for the asymmetric Diels-Alder reactions of anthrones with maleimides. Tetrahedron Asymmetry, 26(24), 1423-1429. https://doi.org/10.1016/j.tetasy.2015.10.022