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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)


Abstract

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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Remarkable Influence of Cobalt Catalysis on Epoxide Ring-Opening with Sulfoxonium Ylides

M. L Jamieson, N. Z. Brant, M. A. Brimble, D. P. Furkert, Synthesis, 2017, 49, 3952-3956.


Key Words

homoallylic alcohols


ID: J54-Y2016