Cooperative coexistence: Effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines

Magnus Rueping*, Cengiz Azap

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

160 Scopus citations

Abstract

A Mannich-aza-Michael reaction in which both an electrophile and a nucleophile are activated provides a simple, highly enantioselective route to isoquinuclidines (1) from imines (2) and cyclohexenone (3). A feature of the reaction is the interplay of an achiral and a chiral Brønsted acid, which enable the asymmetric reaction process by cooperative activation of the enone and the imine. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)7832-7835
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number46
DOIs
StatePublished - Nov 27 2006

Keywords

  • Asymmetric synthesis
  • Ion pairs
  • Isoquinuclidines
  • Mannich bases
  • Michael addition

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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