Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 36, Pages 10755-10759Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201605486
Keywords
atropisomerism; biaryls; enzymes; kinetic resolution; organocatalysis
Categories
Funding
- BBSRC
- EPSRC
- Johnson Matthey Catalysis and Chiral Technologies
- Royal Society Wolfson Research Merit Awards
- Biotechnology and Biological Sciences Research Council [1164625] Funding Source: researchfish
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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.
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