Organic Letters
Organic Letters
5 years ago

Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars

Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars
Sundarababu Baskaran, Akriti Srivastava, Soundararasu Senthilkumar, Sure Siva Prasad
An efficient one-pot method for the stereoselective synthesis of novel iminosugar C-nitromethyl glycosides is described. This new class of iminosugar glycosides has versatile nitromethyl functionality whose utility was further demonstrated in the single-step synthesis of bicyclic iminosugars. Under reagent-free conditions, the N-allyl-C-nitromethyl glycosides resulted in intramolecular cyclization to iminosugar-oximes, whereas under SET oxidation, they furnished cyclopropane-fused iminosugars. The N-propargyl-C-nitromethyl glycosides underwent an unprecedented ketenimine–acrylamidine–Michael addition cascade reaction to give bicyclic amidines.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02175

DOI: 10.1021/acs.orglett.7b02175

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