A facile approach for the asymmetric synthesis of oxindoles with a 3-sulfenyl-substituted quaternary stereocenter

Org Lett. 2013 Oct 4;15(19):4920-3. doi: 10.1021/ol402579x. Epub 2013 Sep 25.

Abstract

With the employment of a threonine-incorporating multifunctional catalyst 9, Michael addition of 3-sulfenyloxindoles to nitroolefins proceeded stereoselectively, leading to the formation of oxindoles with a 3-sulfenyl-substituted quaternary center in excellent yields, and with high diastereoselectivities and excellent enantioselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Nitro Compounds / chemical synthesis*
  • Nitro Compounds / chemistry
  • Oxindoles
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*

Substances

  • Indoles
  • Nitro Compounds
  • Oxindoles
  • Sulfhydryl Compounds
  • 2-oxindole