The role of quinidine in induction of asymmetric synthesis at mercury cathodes

Entrapment of alkaloids within silver: from enantioselective hydrogenation to chiral recognition

“…In our previous research, alkaloids could be electrosorbed to an Ag flake electrode and create a chiral atmosphere for the chiral induction, but this kind of adsorption is reversible and unstable, and alkaloids must be added to the electrolyte every time. 22 Similar results were achieved on the Hg 23 or the Pd 24 electrode. Furthermore, compared to the former work, which reported the highest 17.1% ee and 70% yield in enantioselective hydrogenation using alkaloid@Pd as a catalyst, 19 our work is more effective and avoided the utilization of high pressure hydrogen.…”

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

“…Following the pioneering works by Grimshaw et al [28] in 1973, Gileadi and co-workers showed that the addition of quinidine or related alkaloids to the reaction mixture during the electroreduction of acetophenone on a mercury cathode induces optical activity in the product (alcohol 24a , Scheme 7) [29]. Additionally, pinacol ( 23 ) was also obtained via dimerization along with chiral alcohols.…”

Recent Advances in Asymmetric Catalytic Electrosynthesis

“…The transformation resulted in only modest chiral induction and moderate yields, the latter due to competing dimerization of the intermediate coumarin radical. Nevertheless, the organocatalytic strategy inspired the work of other groups working in this field [81][82][83] and chiral amines have been used as additives in catalytic amounts for asymmetric reduction of various ketones, carboxylic acids and oximes as well as for reductive dehalogenation [84][85][86][87][88][89][90][91][92][93][94][95][96][97]. 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].…”