General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors

Roger Machín Rivera, Yujin Jang, Christopher M. Poteat and Vincent N. G. Lindsay*

*Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States, Email: vlindsancsu.edu

R. M. Rivera, Y. Jang, C. M. Poteat, V. N. G. Lindsay, Org. Lett., 2020, 22, 6510-6515.

DOI: 10.1021/acs.orglett.0c02303

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Abstract

The addition of diverse organometallic reagents to 1-phenylsulfonylcyclopropanols enables a simple and high-yielding synthesis of 1-substituted cyclopropanols. The transformation is amenable to sp-, sp²-, or sp³-hybridized organometallic C-nucleophiles under mild conditions, and the use of enantioenriched substrates led to highly diastereoselective additions.

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Key Words

cyclopropanols, arylation

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ID: J54-Y2020