Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published July 27, 2016 | Accepted Version + Supplemental Material
Journal Article Open

Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams


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 (29.8 MB)
Name Size Download all
19.2 MB Preview Download
6.6 MB Preview Download
3.7 MB Preview Download
275.1 kB Download

Additional details

August 20, 2023
October 20, 2023