Published July 27, 2016
| Accepted Version + Supplemental Material
Journal Article
Open
Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams
Abstract
A new strategy for catalytic enantioselective C-acylation to generate α-quaternary-substituted lactams is reported. Ni-catalyzed three-component coupling of lactam enolates, benzonitriles, and aryl halides produces β-imino lactams that then afford β-keto lactams by acid hydrolysis. Use of a readily available Mandyphos-type ligand and addition of LiBr enable the construction of quaternary stereocenters on α-substituted lactams to form β-keto lactams in up to 94% ee.
Additional Information
© 2016 American Chemical Society. Received: February 25, 2016. Received: February 25, 2016. The authors thank NIH-NIGMS (R01GM080269), Daiichi-Sankyo Co., Ltd. (M.H.), JSPS (S.H.), MEXT (S.H.), the Caltech 3CS, and Caltech for financial support. C.C.E. also thanks Loyola University Chicago for financial support. Mr. Hashiru Negishi (Caltech), Mr. Larry Henling (Caltech), and Dr. Scott Virgil (Caltech) are acknowledged for helpful discussions, instrumentation, and experimental assistance. The authors declare no competing financial interest.Attached Files
Accepted Version - nihms802244.pdf
Supplemental Material - ja6b02120_si_001.pdf
Supplemental Material - ja6b02120_si_002.pdf
Supplemental Material - ja6b02120_si_003.cif
Files
ja6b02120_si_001.pdf
Additional details
- PMCID
- PMC4963289
- Eprint ID
- 69191
- Resolver ID
- CaltechAUTHORS:20160725-104304872
- R01GM080269
- NIH
- Japan Society for the Promotion of Science (JSPS)
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
- Caltech
- Daiichi-Sankyo Co., Ltd.
- Loyola University Chicago
- Created
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2016-07-25Created from EPrint's datestamp field
- Updated
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2022-04-26Created from EPrint's last_modified field