Titanium carbenoid-mediated cyclopropanation of allylic alcohols: selectivity and mechanism
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Author/sDurán-Peña, María Jesús; Botubol Ares, José Manuel; R. Hanson, J.; Hernández Galán, Rosario; González Collado, Isidro
SourceOrganic & Biomolecular Chemistry, 2015, 13, 6325 Received
A new method for the chemo- and stereoselective conversion of allylic alcohols into the corresponding cyclopropane derivatives has been developed. The cyclopropanation reaction was carried out with an unprecedented titanium carbenoid generated in situ from Nugent’s reagent, manganese and methylene diiodide. The reaction involving the participation of an allylic hydroxyl group, proceeded with conservation of the alkene geometry and in a high diastereomeric excess. The scope, limitations and mechanism of this metal-catalysed reaction are discussed.