A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles as progesterone receptor antagonists

S. Alluri, H. Feng, M. Livings, L. Samp, D. Biswas, T. W. Lam, E. Lobkovsky, A. K. Ganguly

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

A convenient enantioselective synthesis of 3-asymmetrically substituted oxindoles is reported. Compound (2) prepared by radical cyclisation of (1) was used for the synthesis of racemic and enantiomerically pure 3-asymmetrically substituted oxindoles. Desulfurisation of (2) using Raney Ni yielded the racemate (5). Addition of (S)-1-phenylethanol to compound (2) yielded the diastereoisomer (21) the structure of which was determined using X-ray crystallography. Using a sequence of steps (21) was converted to the enantiomer (8). The enantiomer (9) was similarly prepared from (2) using (R)-1-phenylethanol.

Original languageEnglish
Pages (from-to)3945-3948
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number30
DOIs
StatePublished - 27 Jul 2011

Keywords

  • Desulfurisation
  • Enantioselective synthesis
  • Progesterone receptor antagonist
  • Radical cyclization

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