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Chemoenzymatic Synthesis of Substituted Azepanes by Sequential Biocatalytic Reduction and Organolithium-Mediated Rearrangement

Author:
Zawodny, Wojciech, Montgomery, Sarah L., Marshall, James R., Finnigan, James D., Turner, Nicholas J., Clayden, Jonathan
Source:
Journal of the American Chemical Society 2018 v.140 no.51 pp. 17872-17877
ISSN:
1520-5126
Subject:
amination, amine oxidase (flavin-containing), amines, imines
Abstract:
Enantioenriched 2-aryl azepanes and 2-arylbenzazepines were generated biocatalytically by asymmetric reductive amination using imine reductases or by deracemization using monoamine oxidases. The amines were converted to the corresponding N′-aryl ureas, which rearranged on treatment with base with stereospecific transfer of the aryl substituent to the 2-position of the heterocycle via a configurationally stable benzyllithium intermediate. The products are previously inaccessible enantioenriched 2,2-disubstituted azepanes and benzazepines.
Agid:
6267646