Biocatalytic Dynamic Kinetic Resolution for the Synthesis of Atropisomeric Biaryl N-Oxide Lewis Base Catalysts

Research output: Contribution to journalArticle

  • External authors:
  • Samantha Staniland
  • Irene Maffucci
  • Alessandro Contini
  • Damian Grainger
  • Jonathan Clayden


Atropisomeric biaryl pyridine and isoquinoline N-oxides were synthesized enantioselectively by dynamic kinetic resolution (DKR) of rapidly racemising precursors exhibiting free bond rotation. The DKR was achieved by ketoreductase (KRED) catalysed reduction of an aldehyde to form a configurationally stable atropisomeric alcohol, with the substantial increase in rotational barrier arising from the loss of a bonding interaction between the N-oxide and the aldehyde. Use of different KREDs allowed either the M or P enantiomer to be synthesized in excellent enantiopurity. The enantioenriched biaryl N-oxide compounds catalyse the asymmetric allylation of benzaldehyde derivatives with allyltrichlorosilane.

Bibliographical metadata

Original languageEnglish
Pages (from-to)10755-10759
Number of pages5
JournalAngewandte Chemie
Issue number36
Early online date9 Aug 2016
Publication statusPublished - 26 Aug 2016

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