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Issue 7, 2020
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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

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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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Article information


Submitted
08 Jan 2020
Accepted
23 Jan 2020
First published
23 Jan 2020

Org. Biomol. Chem., 2020,18, 1343-1348
Article type
Communication

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

R. Sangwan, A. Dubey, A. Tiwari and P. K. Mandal, Org. Biomol. Chem., 2020, 18, 1343
DOI: 10.1039/D0OB00039F

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