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Synlett 2022; 33(12): 1103-1107
DOI: 10.1055/a-1787-1429
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Phosphorus(III)-Promoted 1,2-Boronate Migration and Application to Stereoselective gem-C,B-Glycosylation

Zhi-Tao He∗
We acknowledge financial support from the National Natural Science Foundation of China (NSFC 22071262), the Shanghai Rising-Star program (20QA1411300), CAS Key Laboratory of Synthetic Chemistry of Natural Substances, and the Shanghai Institute of Organic Chemistry.
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Abstract

Modifications of glycosidic linkers are valuable in medicinal chemistry and natural-product synthesis. Whereas considerable attention has been paid to the development of methods for monoglycosylation, the corresponding geminal diglycosylation has almost been ignored. Little work has focused on exploring new routes for stereoselective gem-diglycosylation, presumably due to challenges in controlling selectivity and activity on a confined quaternary carbon center. Highlighted herein is a recent advance in stereoselective C,B-glycosylation through an unprecedented PPh3-promoted 1,2-boronate-migration process.

Key words

diglycosylation - boronate migration - phosphonium ylides - C,B-glycosylation - stereoselectivity


Publication History

Received: 24 February 2022

Accepted after revision: 03 March 2022

Accepted Manuscript online:
03 March 2022

Article published online:
24 March 2022

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