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Asymmetric Reductive Amination/Ring-Closing Cascade: Direct Synthesis of Enantioenriched Biaryl-Bridged NH Lactams
- Source :
- Organic Letters; August 2020, Vol. 22 Issue: 16 p6479-6483, 5p
- Publication Year :
- 2020
-
Abstract
- 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 H2as 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.
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Volume :
- 22
- Issue :
- 16
- Database :
- Supplemental Index
- Journal :
- Organic Letters
- Publication Type :
- Periodical
- Accession number :
- ejs53971783
- Full Text :
- https://doi.org/10.1021/acs.orglett.0c02282