Ortho-quinone methides as reactive intermediates in asymmetric Brønsted acid catalyzed cycloadditions with unactivated alkenes by exclusive activation of the electrophile

Chien Chi Hsiao, Sadiya Raja, Hsuan Hung Liao, Iuliana Atodiresei, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

152 Scopus citations

Abstract

An efficient method for the highly enantioselective synthesis of chiral chromanes bearing multiple stereogenic centers was developed. A chiral BINOL-based N-triflylphosphoramide proved to be an effective catalyst for the in situ generation of ortho-quinone methides (o-QMs) and their subsequent cycloaddition reaction with unactivated alkenes provided chromanes with excellent diastereo- and enantioselectivity. Exclusive chemistry: An efficient method for the highly enantioselective synthesis of chiral chromanes bearing multiple stereogenic centers was developed. A chiral BINOL-based N-triflylphosphoramide proved to be an effective catalyst for the in situ generation of ortho-quinone methides (o-QMs) and their subsequent cycloaddition reaction with unactivated alkenes provided chromanes with excellent diastereo- and enantioselectivity.

Original languageEnglish (US)
Pages (from-to)5762-5765
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number19
DOIs
StatePublished - May 4 2015

Keywords

  • chromanes
  • cycloaddition
  • homogeneous catalysis
  • n-triflylphosphoramide
  • ortho-quinone methide

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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