Non-Covalent Organocatalyzed Domino Reactions Involving Oxindoles: Recent Advances

Molecules. 2017 Sep 29;22(10):1636. doi: 10.3390/molecules22101636.

Abstract

The ubiquitous presence of spirooxindole architectures with several functionalities and stereogenic centers in bioactive molecules has been appealing for the development of novel methodologies seeking their preparation in high yields and selectivities. Expansion and refinement in the field of asymmetric organocatalysis have made possible the development of straightforward strategies that address these two requisites. In this review, we illustrate the current state-of-the-art in the field of spirooxindole synthesis through the use of non-covalent organocatalysis. We aim to provide a concise overview of very recent methods that allow to the isolation of unique, densely and diversified spirocyclic oxindole derivatives with high structural diversity via the use of cascade, tandem and domino processes.

Keywords: cascade; chiral building blocks; domino; enantioselectivity; hydrogen-bonding; non-covalent organocatalysis; spirooxindole derivatives; tandem.

Publication types

  • Review

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cinchona Alkaloids / chemistry
  • Hydrogen Bonding
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Molecular Structure
  • Oxindoles
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Cinchona Alkaloids
  • Indoles
  • Oxindoles
  • Spiro Compounds
  • 2-oxindole