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.brimble
auckland.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
see article for more reactions
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.
see article for more examples
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
