Palladium-Catalyzed Decarboxylative Formal (4 + 2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles

Melissa J. Bird, Steven M. Wales, Christopher Richardson, Christopher J.T. Hyland*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

3 Citations (Scopus)

Abstract

A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H-indolo[2,3-b ]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.

Original languageEnglish
Article numberst-2010-r0641-l
Pages (from-to)916-924
Number of pages9
JournalSYNLETT
Volume31
Issue number9
DOIs
Publication statusPublished - 3 Jun 2020

Bibliographical note

Funding Information:
The authors thank the University of Wollongong and the Australian Research Council (DP180101332) for the generous funding for this research.AustralianResearchCouncil(DP180101332)UniversityofWollongong()

Publisher Copyright:
© 2020. Thieme. All rights reserved.

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

Keywords

  • dearomatization
  • indoles
  • Pd catalysis
  • vinyl benzoxazinanones

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