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Title: Electroreductive generation of (S)-(+)-N,N-dimethyl-2-(hydroxymethyl)- pyrrolidinium mercury compound for enantioselective synthesis of 2-amino-1-alkyl/aryl ethanols
Authors: Yadav, Ashok K
Manju, Meera
Keywords: Enantioselective synthesis;aminoalkyl/aryl ethanols;cathodic reduction;quaternary ammonium amalgams
Issue Date: Dec-2006
Publisher: CSIR
IPC Code: Int.Cl.8C07D
Abstract: (S)-(+)-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 (S)-configuration. The pinacol (racemic/meso) deri­vatives are also isolated as minor products (yield 5-20% ) via dimerization of radical anion followed by protonation.
Page(s): 2770-2772
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(12) December 2006]

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