Sugar-derived cyclic imines: one-pot synthesis and direct functionalization

Sugar-derived cyclic imines: one-pot synthesis and direct functionalization

A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lac...

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Veröffentlicht in:Tetrahedron 2014-03, Vol.70 (10), p.1880-1888
Hauptverfasser: Szcześniak, Piotr, Stecko, Sebastian, Staszewska-Krajewska, Olga, Furman, Bartłomiej
Format: Artikel
Sprache:eng
Schlagworte:
Activation of amides
Amides
Imines
Iminosugars
Nucleophiles
Piperidine
Pyrrolizidines
Reduction
Sugar-derived lactams
Sugars
Synthesis
Tetrahedrons
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Zusammenfassung:A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.01.039