A gold carbene manifold to prepare fused γ-lactams by oxidative cyclisation of ynamides

Paul Davies, Joshua Priest, Fernando Sanchez-Cantalejo

Research output: Contribution to journalArticlepeer-review

20 Citations (Scopus)
132 Downloads (Pure)

Abstract

Gold catalysed oxidative cyclisation reactions of ynamides offer great promise in γ-lactam synthesis but are limited by preferential over-oxidation to form α-keto imides. Evaluating the factors that might limit N-cyclisation pathways led to effective gold-catalysed conditions that allow access to different fused γ-lactams on changing the ynamide N-substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3-aryl indoles and cyclohepta[c]pyrrol-1-one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals.
Original languageEnglish
Pages (from-to)17215-17219
JournalChemistry: A European Journal
Volume24
Issue number65
Early online date24 Sep 2018
DOIs
Publication statusPublished - 22 Nov 2018

Keywords

  • cyclisation
  • gold
  • oxidation
  • ynamide
  • γ-lactam

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry

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