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Synlett 2000; 2000(8): 1199-1201
DOI: 10.1055/s-2000-6743
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Regio- and Stereoselective Intramolecular Cyclization of Some Unconjugated Ketones at Mercury Pool Cathode

Ashok K. Yadav* , Arpita Singh
  • *Department of Chemistry, University of Rajasthan, Jaipur-302 004, India; Fax 0141-51 92 21; E-mail: kudiwal@datainfosys.net
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Publication Date:
31 December 2000 (online)

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This work describes preparative scale electroreductive regio- and stereoselective intramolecular cyclization of some unconjugated ketones at mercury pool cathode in dimethylformamide-2-propanol using tetrabutylammonium fluoroborate as supporting electrolyte and (-)-N,N′-dimethylquininum tetrafluoroborate as a stereo controlled cyclizing agent to yield cis-cyclized products in good yield. Cyclic voltammetric studies have been carried out and a probable mechanism of the process has been presented.

regio-/stereoselectivity - intramolecular cyclization - unconjugated ketones - mercury pool cathode