Synthesis and oxidative cleavage of oxazinocarbazoles: atropselective access to medium-sized rings

Gu Liu, Christopher S. Lancefield, Magali M. Lorion, Alexandra M. Z. Slawin, Nicholas J. Westwood*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Polycyclic systems can be converted into medium-sized-ring-containing compounds through the controlled oxidative cleavage of internal double bonds. This approach is particularly accessible in systems that contain a suitably substituted indole ring. Here, a robust approach to the synthesis of the understudied oxazinocarbazole system is reported. After regioselective incorporation of a carbonyl functional group, m-chloroperoxybenzoic acid (MCPBA) is used to cleave the indole 2,3-double bond that this system contains. This results in a competition between two processes, oxidative cleavage of the double bond and a pinacol-type rearrangement, both of which occur with very high diastereoselectivity. The balance between the two processes is studied as a function of the substrate structure. Extensive use of X-ray crystallographic analysis of the products enables detailed mechanistic conclusions to be drawn.

Original languageEnglish
Pages (from-to)2808-2814
Number of pages7
JournalSynthesis
Volume46
Issue number20
DOIs
Publication statusPublished - Oct 2014

Keywords

  • atropisomerism
  • diastereoselectivity
  • macrocycles
  • epoxidation
  • heterocycles
  • Chloroperbenzoic acid
  • Asymmetric-Synthesis
  • Superquat enamides
  • Functionalization
  • Inhibitors
  • Strategy
  • MCPBA

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