Kinetic resolution of tertiary alcohols by chiral DMAP derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles

Hiroki Mandai, Ryuhei Shiomoto, Kazuki Fujii, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journalArticlepeer-review

Abstract

We developed an efficient acylative kinetic resolution of 3-hydroxy-3-substituted 2-oxindoles by a chiral DMAP derivative having a 1,1′-binaphthyl with two tert-alcohols units. A wide range of 3-hydroxy-3-substituted oxindoles having various functional groups were efficiently resolved (14 examples, up to s = 60) in the presence of 1 mol % of catalyst within 3−9 h. Multigram-scale reactions (10 g) also proceeded with a high s-factor (s = 43) within 5 h.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusAccepted/In press - 2021

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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