American Chemical Society
Browse
ja6b02120_si_002.pdf (6.26 MB)

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

Download (6.26 MB)
journal contribution
posted on 2016-07-03, 00:00 authored by Masaki Hayashi, Shoshana Bachman, Satoshi Hashimoto, Chad C. Eichman, Brian M. Stoltz
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.

History