Asymmetric brønsted acid catalyzed nucleophilic addition to in situ generated chiral N-acyliminium ions

Magnus Rueping*, Boris J. Nachtsheim

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

87 Scopus citations

Abstract

A new enantioselective Brønsted acid catalyzed nucleophilic substitution of γ-hydroxylactams with indole is presented. The reaction proceeds via an intermediary N-acyliminium ion and provides disubstituted γ-lactams in good yields and with high enantioselectivities.

Original languageEnglish (US)
Pages (from-to)119-122
Number of pages4
JournalSynlett
Issue number1
DOIs
StatePublished - 2010
Externally publishedYes

Keywords

  • Amino acid
  • Nucleophilic substitution
  • Organocatalysis
  • Protonation
  • Quaternary stereocenter

ASJC Scopus subject areas

  • Organic Chemistry

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