Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Biocatalytic Routes to Enantiomerically Enriched Dibenz[c,e]azepines

Scott P France, Nicholas John Turner, Jeremy Steflik, Iustina Slabu, Roger M Howard, Mahima Sharma, Godwin A Aleku, Ralph W Adams, Rajesh Kumar, Timothy W Wallace, Gideon Grogan, Robert Crook, Juan Mangas-Sanchez
Biocatalytic retrosynthetic analysis of dibenz[c,e]azepines has highlighted the use of imine reductase (IRED) and w-transaminase (w-TA) biocatalysts to establish the key stereocentres of these molecules. Several enantiocomplementary IREDs were identified for the synthesis of (R)- and (S)-5-methyl-6,7-dihydro-5H-dibenz[c,e]azepine with excellent enantioselectivity by reduction of the parent imines. Crystallographic evidence suggests that IREDs may be able to bind one conformer of the imine substrate such that, upon reduction, the major product conformer is generated directly. ω-TA biocatalysts were also successfully employed for the production of enantiopure 1-(2-bromophenyl)ethan-1-amine enabling an orthogonal route for the installation of chirality into dibenz[c,e]azepine frameworks.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708453

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