Chiral organic contact ion pairs in metal-free catalytic asymmetric allylic substitutions

Magnus Rueping*, Uxue Uria, Ming Yuan Lin, Iuliana Atodiresei

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

184 Scopus citations

Abstract

Chiral contact ion-pair catalysis with particular focus on metal-free processes is gaining in interest. As a result, new perspectives are opened, and highly stereoselective transformations, traditionally performed under metal catalysis, can be realized. Herein, we report the development of an unprecedented asymmetric Brønsted acid-catalyzed allylic alkylation. The concept relies on chiral contact ion-pair catalysis, in which the chiral organic counteranion of an allylic carbocation induces high enantioselectivities and allows access to biologically relevant chromenes in good yields and with excellent enantioselection.

Original languageEnglish (US)
Pages (from-to)3732-3735
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number11
DOIs
StatePublished - Mar 23 2011

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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