Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins

Madhu Chennapuram, U. V. Subba Reddy, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A series of hybrid-type squaramide-fused amino alcohol (SFAA) catalysts were synthesized, and their catalytic efficiency in the enantioselective nitro-aldol reaction of various isatins with nitromethane has been described. This transformation afforded chiral 3-substituted 3-hydroxyoxindoles in excellent chemical yields (up to 99 %) with high enantioselectivities (up to 95 % ee). The resulting chiral 3-hydroxyoxindoles can be further used as synthetic precursors for the synthesis of several natural products that have a broad spectrum of fascinating biological activities.

Original languageEnglish
Pages (from-to)1638-1646
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number12
DOIs
Publication statusPublished - 2017 Mar 27

Keywords

  • Amino alcohols
  • Asymmetric catalysis
  • Enantioselectivity
  • Nitro-aldol reaction
  • Organocatalysts

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins'. Together they form a unique fingerprint.

Cite this