Chiral Brøsted acids in the catalytic asymmetric nazarov cyclization - The first enantioselective organocatalytic electrocyclic reaction

Magnus Rueping*, Winai Ieawsuwan, Audrey P. Antonchick, Boris J. Nachtsheim

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

238 Scopus citations

Abstract

(Chemical Equation Presented) Low catalyst loadings, high enantioselectivities, mild conditions, and fast reaction times are the important features of the first enantioselective organocatalytic electrocyclic reaction: a Nazarov cyclization leading to the synthesis of substituted five-membered rings with a chiral Bransted acid as a catalyst (see scheme). A further advantage of this method is the possible entry to all four diastereomers of the product.

Original languageEnglish (US)
Pages (from-to)2097-2100
Number of pages4
JournalAngewandte Chemie - International Edition
Volume46
Issue number12
DOIs
StatePublished - Jun 29 2007

Keywords

  • Binol phosphate
  • Brønsted acids
  • Electrocyclization
  • Ion-pair catalysis
  • Nazarov cyclization

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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