首页|One-Pot Stereoselective Synthesis of Different Fused Multicyclic Iminosugars Based on the Iminium-lon Intermediate
One-Pot Stereoselective Synthesis of Different Fused Multicyclic Iminosugars Based on the Iminium-lon Intermediate
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Different novel fused multicyclic iminosugars were synthesized from D-ribose tosylate,aniline and vinyl ethyl ether by one-pot three-component stereoselective[4+2]reaction at different temperatures.The iminium-ion is the key intermediate for the reaction.As a result,several complex fused iminosugars 3a were obtained by aza-Diels-Alder mechanism at 60 ℃,while a series of aza-C-glycosides 5a were prepared by Mannich reaction at room temperature accompanied by another tetrahydroquinoline-fused iminosugars 4a(tricyclic derivatives)through aza-Diels-Alder cycloaddition.This strategy will help to construct structurally diverse and bioactive iminosugar analogues.
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