Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 19, Pages 11860-11872Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01763
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Funding
- NSERC (Discovery Grants and Canada Research Chairs programs)
- Canada Foundation for Innovation [35261]
- Ontario Research Fund
- University of Toronto
- Ontario for a graduate scholarship (OGS)
- NSERC
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A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)(2). Alkene additives were found to inhibit catalysis, suggesting that avoiding beta-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (+/-)-naproxen from commercially available starting materials.
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