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The strategic use of para-quinone methides to access synthetically challenging and chemoselective α,α′-diarylmethyl N-glycosides from unprotected carbohydrate amines†
Atul Dubey,Ashwani Tiwari
Organic & Biomolecular Chemistry Pub Date : 01/23/2020 00:00:00 , DOI:10.1039/D0OB00039F
Abstract

Reported herein is a practical route to access synthetically challenging and chemoselective α,α′-diarylmethyl N-glycosides via Sc(OTf)3-catalyzed 1,6-conjugate addition of amino sugars with para-quinone methides (p-QMs). The reactions proceed smoothly without a base and under mild reaction conditions with a broad substrate scope and moderate to good yields.

Graphical abstract: The strategic use of para-quinone methides to access synthetically challenging and chemoselective α,α′-diarylmethyl N-glycosides from unprotected carbohydrate amines
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