Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones

Jo Kimura, Ummareddy Venkata Subba Reddy, Yoshihito Kohari, Chigusa Seki, Yasuteru Mawatari, Koji Uwai, Yuko Okuyama, Eunsang Kwon, Michio Tokiwa, Mitsuhiro Takeshita, Tatsuo Iwasa, Hiroto Nakano

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Enantioselective aldol reactions of various isatins with ketones using newly designed amino amide organocatalysts were found to provide chiral 3-substituted 3-hydroxy-2-oxindoles in good to excellent yields and with excellent stereoselectivities (up to 99 %, up to 98 % ee, syn/anti = 99:1); one catalyst, 3i, proved particularly successful. One of the resulting oxindoles, 3-hydroxy-3-(2-oxocyclohexyl)-2-indolinone may serve as a synthetic intermediate for pharmaceutically important compounds and, in its own right, shows interesting anticonvulsant activities.

Original languageEnglish
Pages (from-to)3748-3756
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number22
DOIs
Publication statusPublished - 2016

Keywords

  • 3-Hydroxy-2-oxindole
  • Aldol reactions
  • Amino amide
  • Enantioselectivity
  • Isatin
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Kimura, J., Subba Reddy, U. V., Kohari, Y., Seki, C., Mawatari, Y., Uwai, K., Okuyama, Y., Kwon, E., Tokiwa, M., Takeshita, M., Iwasa, T., & Nakano, H. (2016). Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones. European Journal of Organic Chemistry, 2016(22), 3748-3756. https://doi.org/10.1002/ejoc.201600414