Organo-zinc Promoted Diastereoselective C-Arylation of 1,2-Anhydrosugars from Arylboronic Acids

Organic Letters
Madhu Babu TatinaDebaraj Mukherjee

Abstract

α-C-arylglycosides can be obtained through the addition of aryl zinc reagents to sugar epoxides. The required aryl zinc nucleophiles can be easily obtained from the corresponding boronic acids by B-Zn exchange and attack sugar 1,2 epoxides in a highly diastereoselective fashion to generate 1,2-cis-α-hexapyranosyl aryl glycosides under ligand- and base-free conditions.

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Citations

Jan 23, 2016·Organic Letters·Anthony W McDonaghPaul V Murphy
Jan 19, 2017·Journal of the American Chemical Society·Guillaume Benoit, André B Charette

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