Conjugate Addition of 3‐Aryl Oxindoles to <i>In Situ</i> Generated <i>o</i>–Quinone Methides Without Essential Electronic or Steric Groups

Abstract Herein an efficient method for in situ generated o –quinone methides without essential electronic or steric groups at the exocyclic methylene or on six‐membered ring was established. The method relies on acetylation of salicylylols and subsequently base promoted 1,4‐elimination. The in situ generated o –quinone methides could be undergoing conjugate addition with 3‐aryl oxindoles in one‐pot reaction system, which provided 3,3‐disubstituted oxindoles bearing a quaternary stereocenter in good yields (up to 99 %).

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2024-10-08
DOI
https://doi.org/10.1002/ajoc.202400370
Citations
1
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
0.25
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article

Conjugate Addition of 3‐Aryl Oxindoles to In Situ Generated o–Quinone Methides Without Essential Electronic or Steric Groups

Liu Song
1 citations
Asian Journal of Organic Chemistry
Synthesis of Indole Derivatives
0.25
article

Conjugate Addition of 3‐Aryl Oxindoles to In Situ Generated o–Quinone Methides Without Essential Electronic or Steric Groups

Liu Song
article en
1 citations

Abstract

Abstract Herein an efficient method for in situ generated o –quinone methides without essential electronic or steric groups at the exocyclic methylene or on six‐membered ring was established. The method relies on acetylation of salicylylols and subsequently base promoted 1,4‐elimination. The in situ generated o –quinone methides could be undergoing conjugate addition with 3‐aryl oxindoles in one‐pot reaction system, which provided 3,3‐disubstituted oxindoles bearing a quaternary stereocenter in good yields (up to 99 %).

Asian Journal of Organic ChemistryVol. 13(12)
Chongqing University of Science and Technology (CN), Chongqing University of Technology (CN)
Openalex Percentile: Top 48%
Synthesis of Indole Derivatives
0.25
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