Electroreductive generation of (<i>S</i>)-(+)-N,N-dimethyl-2-(hydroxymethyl)- pyrrolidinium mercury compound for enantioselective synthesis of 2-amino-1-alkyl/aryl ethanols

Abstract

(<i>S</i>)-(+)-N, N - Dimethyl-2-(hydroxymethyl)-pyrrolidinium (DMHP⁺)-mercury compound mediated enantioselective reduction of aminomethyl alkyl/aryl ketones in dimethyl­formamide-2-propanol (9:1) has been carried out using tetra­butylammonium tetrafluoroborate as a supporting electrolyte. The products viz. 2-amino-1-alkyl/aryl ethanols have been obtained in good yield (68-92%) with 35-91% optical purity and have been assigned (<i>S</i>)-configuration. The pinacol (racemic/meso) deri­vatives are also isolated as minor products (yield 5-20% ) via dimerization of radical anion followed by protonation.