Electrochemical Reduction of a Racemic Allyl β-Keto Ester Catalyzed by Nickel Complexes: Asymmetric Induction

Abstract

The nickel-catalyzed electroreductive cleavage of the allyl group of allyl 2-methyl-1-tetralone-2-carboxylate and allyl transfer to the carbonyl group has been examined. The control of the reaction conditions allowed us to orientate the se-

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…Deprotection of allyl carbonates using this system has also been described. 662 Hudlicky and co-workers found that cinnamyl group exhibited lower reduction potentials (absolute value) compared to simple allyl groups. Cinnamyl ethers could, therefore, be reduced without a nickel mediator.…”

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

“…Constant current electrolysis of 89 in a single compartment cell using a sacrificial Mg anode was conducted in the presence of a Ni catalyst and chiral ligand 90 . After esterification and purification, 91 was isolated in a good yield and with moderate enantioselectivity [70].…”

Recent Advances in Asymmetric Catalytic Electrosynthesis

“…Electrocatalytic reductions have also been carried out using metal catalysts, including a Rh III polypyridyl complex for the hydrogenation of acetophenone with modest chiral induction [98]. Other early electroreductive metal-catalyzed enantioselective processes include cobalt catalysis in the form of vitamin B 12 [99][100][101] , as well as nickel catalysis [102] for dehalogenations, isomerizations, reductive cleavages, etc.…”