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

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

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

6 Citations (Scopus)
78 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)17872–17877
Number of pages6
JournalJournal of the American Chemical Society
Volume140
Issue number51
Early online date6 Dec 2018
DOIs
Publication statusPublished - 26 Dec 2018

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