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Wiley, Angewandte Chemie International Edition, 36(55), p. 10755-10759

DOI: 10.1002/anie.201605486

Wiley, Angewandte Chemie, 36(128), p. 10913-10917, 2016

DOI: 10.1002/ange.201605486

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

Journal article published in 2016 by Samantha Staniland, Ralph W. Adams, Joseph J. W. Mcdouall ORCID, Irene Maffucci, Alessandro Contini, Damian M. Grainger, Nicholas J. Turner, Jonathan Clayden ORCID
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This paper is available in a repository.

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Abstract

Atropisomeric biaryl pyridine and isoquinoline N-oxides were synthesized enantioselectively by dynamic kinetic resolution (DKR) of rapidly racemizing precursors exhibiting free bond rotation. The DKR was achieved by ketoreductase (KRED) catalyzed 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 catalyze the asymmetric allylation of benzaldehyde derivatives with allyltrichlorosilane.