Grignard addition to imines derived from isatine: a method for the asymmetric synthesis of quaternary 3-aminooxindoles

J Org Chem. 2009 Jun 19;74(12):4537-41. doi: 10.1021/jo900623c.

Abstract

Addition of Grignard reagents to chiral imines derived from isatine afforded chiral, optically enriched 3-substituted 3-aminooxindoles in satisfactory yields and diastereoisomeric ratios. A general protocol is described for the addition of alkyl, alkenyl, and aryl Grignard reagents. In one case, the absolute configuration at C3 was determined and the selective N-deprotection was described, enabling further synthetic transformations of the reaction product.

MeSH terms

  • Imines / chemistry*
  • Indoles / chemical synthesis*
  • Quaternary Ammonium Compounds / chemical synthesis*
  • Stereoisomerism

Substances

  • Imines
  • Indoles
  • Quaternary Ammonium Compounds