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

Research output: Contribution to journalArticle

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
DateAccepted/In press - 6 Dec 2018
DateE-pub ahead of print - 6 Dec 2018
DatePublished (current) - 26 Dec 2018

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.

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    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at https://pubs.acs.org/doi/10.1021/jacs.8b11891 . Please refer to any applicable terms of use of the publisher.

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