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Synlett 2000; 2000(4): 467-470
DOI: 10.1055/s-2000-6572
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Synthesis of Hydroxypiperidines Using 1,4-Ditosyltetrahydropyridines

Jean-Claude Adelbrecht* , Donald Craig, Brian W. Dymock, Serge Thorimbert
  • *Centre for Chemical Synthesis, Department of Chemistry, Imperial College of Science, Technology and Medicine, London SW7 2AY, UK; Fax +44 20 75 94 58 68; E-mail: d.craig@ic.ac.uk
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Publication Date:
31 December 2000 (online)

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Dihydroxylation of diastereomerically pure 2-alkyl 1,4-ditosyl-1,2,3,4-tetrahydropyridines occurs with complete stereoselectivity to give the corresponding diols. Upon treatment with nucleophile - Lewis acid mixtures the derived diacetates undergo substitution reactions whose selectivity varies according to the steric bulk of the alkyl substituent.

diols - Lewis acids - piperidines - pyridines - stereoselectivity