Asymmetric Reductive Amination/Ring-Closing Cascade: Direct Synthesis of Enantioenriched Biaryl-Bridged NH Lactams

We report here a Ru-catalyzed enantioselective synthesis of biaryl-bridged NH lactams through asymmetric reductive amination and a spontaneous ring-closing cascade from keto esters and NH4OAc with H2 as reductant. The reaction features broad substrate generality and high enantioselectivities (up to...

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Bibliographic Details
Published in:Organic letters 2020-08, Vol.22 (16), p.6479-6483
Main Authors: Zhang, Yao, Liu, Yun-Qi, Hu, Le’an, Zhang, Xumu, Yin, Qin
Format: Article
Language:English
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Summary:We report here a Ru-catalyzed enantioselective synthesis of biaryl-bridged NH lactams through asymmetric reductive amination and a spontaneous ring-closing cascade from keto esters and NH4OAc with H2 as reductant. The reaction features broad substrate generality and high enantioselectivities (up to >99% ee). To showcase the practical utility, a highly enantioselective synthesis of 5-ethylindolobenzazepinone C, a promising antimitotic agent, has been rapidly completed. Furthermore, the amide group in the products enables versatile elaborations through directed C–H functionalization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02282