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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.45B [2006] >
IJC-B Vol.45B(12) December 2006] >
| 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) |
| Source: | IJC-B Vol.45B(12) December 2006]
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