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

2018; American Chemical Society; Volume: 140; Issue: 51 Linguagem: Inglês

10.1021/jacs.8b11891

1943-2984

Wojciech Zawodny, Sarah L. Montgomery, James R. Marshall, James Finnigan, Nicholas J. Turner, Jonathan Clayden,

Asymmetric Hydrogenation and Catalysis

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.