Abstract

Deoxygalactostatin, homogalactonojirimycin derivatives and other 2,6-imino-heptitols are accessed via the nucleophilic addition of a hydroxymethyl anion equivalent to 5-azido-1,4-lactones to afford 6-azido-lactols. Subsequent hydrogenation induces intramolecular reductive amination to produce the desired piperidine ring systems.

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