Asymmetric Brønsted acid catalysis: Enantioselective nucleophilic substitutions and 1,4-additions

Magnus Rueping*, Boris J. Nachtsheim, Stefan A. Moreth, Michael Bolte

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

303 Scopus citations

Abstract

(Chemical Equation Presented) Executive decision: Depending on the catalyst (both N-triflylphosphoramides), the highly enantioselective Brønsted acid catalyzed addition of indoles to α,β-unsaturated carbonyl compounds provides either α-keto esters (up to 92% ee, left side of the scheme), or a novel type of bisindole (right), which displays atropisomerism. The α-keto esters can also be converted into amino acids by a one-pot 1,4-addition-reductive amination reaction.

Original languageEnglish (US)
Pages (from-to)593-596
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number3
DOIs
StatePublished - 2008
Externally publishedYes

Keywords

  • Alkylation
  • Atropisomers
  • Michael addition
  • Nucleophilic substitution
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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