ja6b02120_si_002.pdf (6.26 MB)
Ni-Catalyzed Enantioselective C‑Acylation of α‑Substituted Lactams
journal contribution
posted on 2016-07-03, 00:00 authored by Masaki Hayashi, Shoshana Bachman, Satoshi Hashimoto, Chad C. Eichman, Brian M. StoltzA 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.