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Cyclopropanols_Lindsay_MANUSCRIPT.pdf (1.51 MB)
General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 11.07.2020 and posted on 13.07.2020by Roger Machín Rivera, Yujin Jang, Christopher M. Poteat, Vincent Lindsay
The 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 only received very little attention in the literature for the formation of tertiary cyclopropanols. In this work, we
report a simple and high-yielding synthesis 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.