Combining biocatalytic oxyfunctionalisation and organocatalytic aldol reaction to access chiral β-hydroxy ketones

Yutong Wang, Chiara Domestici, Niklas Teetz, Dirk Holtmann, Miguel Alcalde, Mengfan Wang, Wei Qi, Wuyuan Zhang, Frank Hollmann*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

24 Downloads (Pure)

Abstract

This study explores a chemoenzymatic cascade to synthesise chiral β-hydroxy ketones by integrating the selective oxyfunctionalisation capabilities of peroxygenases with the carbon-carbon bond-forming progress of organocatalysts. Initial results with simple organocatalysts demonstrated poor performance due to mutual inactivation of the biocatalyst and organocatalyst. However, the use of more complex prolinamide derivatives improved the reaction efficiency and enantioselectivity, enabling a one-pot, one-step synthesis process. This methodology was further optimised to produce high yields of enantiomerically pure aldol products and was shown to be extendable to other substituted toluenes and aldol donors.
Original languageEnglish
Article number114515
Number of pages5
JournalMolecular Catalysis
Volume569
DOIs
Publication statusPublished - 2024

Keywords

  • Asymmetric aldol reaction
  • Chemoenzymatic cascade
  • Organocatalysis
  • Oxyfunctionalisation
  • Peroxygenase

Fingerprint

Dive into the research topics of 'Combining biocatalytic oxyfunctionalisation and organocatalytic aldol reaction to access chiral β-hydroxy ketones'. Together they form a unique fingerprint.

Cite this