Divergent Reactivity via Cobalt Catalysis: An Epoxide Olefination
Megan L. Jamieson, Paul A. Hume, Daniel P. Furkert* and Margaret A. Brimble*
*School of Chemical Sciences and Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, 23 Symonds Street, Auckland 1142, New Zealand, Email: d.furkertauckland.ac.nz., m.brimbleauckland.ac.nz.
M. L. Jamieson, P. A. Hume, D. P. Furkert, M. A. Brimble, Org. Lett., 2016, 18, 468-471.
DOI: 10.1021/acs.orglett.5b03514 (free Supporting Information)
In the presence of a cobalt catalyst, the reaction of epoxides with dimethylsulfoxonium methylide delivers homoallylic alcohols instead of oxetanes. The observed reactivity change appears to be specifically due to cobalt salts and is broadly applicable to a variety of epoxides, retaining the initial stereochemistry.
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M. L Jamieson, N. Z. Brant, M. A. Brimble, D. P. Furkert, Synthesis, 2017, 49, 3952-3956.