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Enantioselective cathodic reduction of some prochiral ketones in the presence of (−)-N,N′-dimethylquininium tetrafluoroborate at mercury cathode

✍ Scribed by Ashok K. Yadav; Meera Manju; Pukh Raj Chhinpa


Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
108 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis


This work describes preparative scale enantioselective cathodic reduction of some prochiral ketones, viz. 3,4-dihydro-1(2H)-naphthaleneone, 2-octanone, 1-phenyl-2-propanone, E-3-octen-2-one, 1-octyn-3-one, 1-undecyn-3-one, 1-tetradecyn-3-one at mercury pool in N,N-dimethyl formamide (DMF)-2-propanol (9.5:0.5), using tetrabutylammonium tetrafluoroborate (TBA•BF 4 ), as supporting electrolyte and (-)-N,N%-dimethylquininium tetrafluoroborate (DMQ•2BF 4 ), as a enantioselective inductor. The products obtained were corresponding (S)-alcohols in 24-70% ee.


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