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

研究成果: Article査読

24 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3748-3756
ページ数9
ジャーナルEuropean Journal of Organic Chemistry
2016
22
DOI
出版ステータスPublished - 2016 8月

ASJC Scopus subject areas

  • 物理化学および理論化学
  • 有機化学

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