Site- and Enantioselective C−H Oxygenation Catalyzed by a Chiral Manganese Porphyrin Complex with a Remote Binding Site

Finn Burg, Maxime Gicquel, Stefan Breitenlechner, Alexander Pöthig, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

87 Scopus citations

Abstract

A chiral manganese porphyrin complex with a two-point hydrogen-bonding site was prepared and probed in catalytic C−H oxygenation reactions of 3,4-dihydroquinolones. The desired oxygenation occurred with perfect site selectivity at the C4 methylene group and with high enantioselectivity in favor of the respective 4S-configured secondary alcohols (12 examples, 29–97 % conversion, 19–68 % yield, 87–99 % ee). Mechanistic studies support the hypothesis that the reaction proceeds through a rate- and selectivity-determining attack of the reactive manganese oxo complex at the hydrogen-bound substrate and an oxygen transfer by a rebound mechanism.

Original languageEnglish
Pages (from-to)2953-2957
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume57
Issue number11
DOIs
StatePublished - 5 Mar 2018

Keywords

  • enantioselectivity
  • hydrogen bonds
  • manganese
  • oxygenation
  • porphyrinoids

Fingerprint

Dive into the research topics of 'Site- and Enantioselective C−H Oxygenation Catalyzed by a Chiral Manganese Porphyrin Complex with a Remote Binding Site'. Together they form a unique fingerprint.

Cite this