ol0c02303_si_001.pdf (8.95 MB)
General Synthesis of Cyclopropanols via Organometallic Addition to 1‑Sulfonylcyclopropanols as Cyclopropanone Precursors
journal contribution
posted on 2020-08-06, 22:20 authored by Roger
Machín Rivera, Yujin Jang, Christopher M. Poteat, Vincent N. G. LindsayThe addition of organometallic
reagents to ketones constitutes
one of the most straightforward synthetic approaches to tertiary alcohols.
However, due to the absence of a well-behaved class of cyclopropanone
surrogates accessible in enantioenriched form, such a trivial synthetic
disconnection has received very little attention in the literature
for the formation of tertiary cyclopropanols. In this work, we report
a simple and high-yielding synthesis of 1-substituted cyclopropanols
via the addition of diverse organometallic reagents to 1-phenylsulfonylcyclopropanols,
acting here as in situ precursors of the corresponding cyclopropanones.
The transformation is shown to be amenable to sp-, sp2-,
or sp3-hybridized organometallic C-nucleophiles under mild
conditions, and the use of enantioenriched substrates led to highly
diastereoselective additions and the formation of optically active
cyclopropanols.