Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters
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 β-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.
Michel, Nicholas W. M.,Jeanneret, Alexandria D. M.,Kim, Hyehwang,Rousseaux, Sophie A. L.
p. 11860 - 11872
(2018/10/02)
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