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Synlett 2001; 2001(3): 0421-0423
DOI: 10.1055/s-2001-11412
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Cobaloxime-Mediated Intramolecular Radical Addition onto Oxime Functions in the Electrolysis Media: Formation of Mannich Base Analogues

Tsutomu Inokuchi* , Hiroyuki Kawafuchi
  • *Department of Bioscience and Biotechnology, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan; Fax + 81-86-2 51-80 21; E-mail: inokuchi@biotech.okayama-u.ac.jp
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Publication Date:
31 December 2001 (online)

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Addition of the carbon radical generated from α-bromoacetals onto the O-alkyloximes, affording Mannich base analogues, was achieved by the electrolysis in MeOH containing cobaloxime (catalytic) as a mediator at a Zn sacrificial electrode in an undivided cell. Cyclization proceeded stereoselectively in some cases to afford the 2-alkoxy-3-alkyl-4-aminotetrahydrofurans.

acetals - amines - cyclization - ring closure - radical reactions

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