ol9b03435_si_002.pdf (4.82 MB)
Ni-Catalyzed β‑Alkylation of Cyclopropanol-Derived Homoenolates
journal contribution
posted on 2019-10-18, 20:03 authored by L. Reginald Mills, Cuihan Zhou, Emily Fung, Sophie A. L. RousseauxMetal homoenolates
are valuable synthetic intermediates which provide
access to β-functionalized ketones. In this report, we disclose
a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived
homoenolates using redox-active N-hydroxyphthalimide
(NHPI) esters as the alkylating reagents. The reaction is compatible
with 1°, 2°, and 3° NHPI esters. Mechanistic studies
imply radical activation of the NHPI ester and 2e β-carbon elimination
occurring on the cyclopropanol.