Gold-catalyzed asymmetric allylic substitution of free alcohols: An enantioselective approach to chiral chromans with quaternary stereocenters for the synthesis of Vitamin E and analogues

Uxue Uria, Carlos Vila, Ming Yuan Lin, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

The enantioselective synthesis of α- and γ-tocopherol (the most biologically active members of vitamin E family) and analogues has been accomplished employing a new enantioselective gold catalyzed intramolecular allylic alkylation reaction followed by an olefin cross-metathesis as key steps. The methodology proved to be applicable to different olefins highlighting its potential for the synthesis of diverse libraries. The enantioselective synthesis of α- and γ-tocopherol (the most biologically active members of vitamin E family) and analogues has been accomplished employing an enantioselective gold-catalyzed intramolecular allylic alkylation reaction followed by an olefin cross-metathesis as key steps (see scheme).

Original languageEnglish (US)
Pages (from-to)13913-13917
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number43
DOIs
StatePublished - Oct 20 2014

Keywords

  • Vitamin E
  • allylic alkylation
  • chromans
  • gold catalysis
  • tocopherol

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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