Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 51, Pages 17872-17877Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b11891
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Funding
- BBSRC
- EPSRC
- ERC
- Prozomix Ltd.
- Johnson Matthey
- EPSRC [EP/K03927X/1, EP/L018527/2] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1] Funding Source: researchfish
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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 stereo specific 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 benzaze-pines.
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