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

4 Citations (Scopus)

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
Pages (from-to)1169-1174
Number of pages6
JournalOrganic Letters
Volume23
Issue number4
DOIs
Publication statusPublished - Feb 19 2021

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles'. Together they form a unique fingerprint.

Cite this