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Synlett 2000; 2000(2): 193-196
DOI: 10.1055/s-2000-6499
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A Convenient Synthesis of N-substituted Trihydroxypiperidines from Bis-Epoxides: Nucleophilic Opening of 1,2:4,5-Dianhydropentitols

Rachel D. Smith* , Neil R. Thomas
  • *School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK; E-mail: Neil.Thomas@Nottingham.ac.uk
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Publication Date:
31 December 2000 (online)

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Synthesis of a number of N-substituted trihydroxypiperidine and trihydroxypyrrolidines is described via the nucleophilic opening and cyclisation of suitable bis-epoxides. Reaction conditions to maximise the yield of the trihydroxypiperidine products formed by a 6-endo-tet cyclisation process are provided.

aza-sugar - imino sugar - bis-epoxide - glycosidase inhibitor - isofagomine