Experimental and computational study of the catalytic asymmetric 4π-electrocyclization of N-heterocycles

Sadiya Raja, Masaki Nakajima, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

The first asymmetric metal-catalyzed Nazarov cyclization of N-heterocycles has been developed. The use of a chiral catalyst allows the enantioselective electrocyclization of N-heterocycles under mild conditions and the corresponding products are obtained in good yields with excellent enantio- and diastereoselectivity. The reaction mechanism and the absolute configuration of the obtained products are explained by means of computational studies.

Original languageEnglish (US)
Pages (from-to)2762-2765
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number9
DOIs
StatePublished - Feb 23 2015

Keywords

  • Electrocyclization
  • Indole alkaloids
  • Lewis acid catalysis
  • Nazarov reaction

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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