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

Megan L. Jamieson, Nicola Z. Brant, Margaret A. Brimble*, Daniel P. Furkert*

*School of Chemical Sciences and Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, 23 Symonds Street, Auckland 1142, New Zealand, Email: m.brimbleauckland.ac.nz, d.furkertauckland.ac.nz

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

DOI: 10.1055/s-0036-1588814 (free Supporting Information)


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Abstract

An expanded survey of transition-metal catalysts has confirmed that cobalt salts uniquely deliver homoallylic alcohol products from epoxides, with retention of the original epoxide stereochemistry. A tandem Corey-Chaykovsky/epoxide olefination sequence gives homoallylic alcohols from aldehydes.

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Divergent Reactivity via Cobalt Catalysis: An Epoxide Olefination

M. L. Jamieson, P. A. Hume, D. P. Furkert, M. A. Brimble, Org. Lett., 2016, 18, 468-471.


Key Words

Corey-Chaykovsky reaction, cobalt catalysis, diverted reactivity, epoxide olefination, carbon-carbon bond formation, oxetane, Jacobsen HKR, homoallylic alcohols


ID: J66-Y2017