Unifying metal- and organocatalysis for asymmetric oxidative iminium activation: A relay catalytic system enabling the combined allylic oxidation of alcohols and prolinol ether catalyzed iminium reactions

Magnus Rueping*, Henrik Sundén, Erli Sugiono

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

A multicatalytic system consisting of tetrapropylammonium perruthenate/N-methylmorpholine N-oxide (TPAP/NMO) as oxidant, and diarylprolinol TMS-ether as chiral amine catalyst, has been developed and applied in the efficient construction of valuable chiral molecules. The one-pot domino reactions elaborated in the present study are based on the in situ generation of α,β-unsaturated aldehydes from allylic alcohols and their subsequent use in various asymmetric transformations (e.g., cyclopropanation, Michael addition, Michael addition/acetalization). TPAP as a substrate-selective redox catalyst is well tolerated by the amine catalyst and the domino reactions proceed in good yields and high enantioselectivities. The compatibility of metal and organocatalysis presented herein widens the scope of asymmetric iminium catalysis.

Original languageEnglish (US)
Pages (from-to)3649-3653
Number of pages5
JournalChemistry - A European Journal
Volume18
Issue number12
DOIs
StatePublished - Mar 19 2012

Keywords

  • asymmetric catalysis
  • cascade reactions
  • iminium activation
  • oxidation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Unifying metal- and organocatalysis for asymmetric oxidative iminium activation: A relay catalytic system enabling the combined allylic oxidation of alcohols and prolinol ether catalyzed iminium reactions'. Together they form a unique fingerprint.

Cite this