An improved synthetic route to enantio- and diastereoenriched iodocyclopropylmethanols, using (diiodomethyl)zinc iodide etherate as the active species, is described. The products obtained by this methodology were successfully functionalized by Suzuki-Miyaura cross-coupling reactions. A Buchwald-type palladium precatalyst allowed access to highly substituted and stereo-enriched cyclopropanes without requiring a protecting group.

Spectroscopic characterization of diiodomethylzinc iodide: Application to the stereoselective synthesis and functionalization of iodocyclopropanes

255th National Meeting (2018)

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