Tris(pentafluorophenyl)borane-Catalyzed Stereoselective C-Glycosylation of Glycals: A Facile Synthesis of Allyl and Alkynyl Glycosides

Abstract

In modern advances, tris(pentafluorophenyl)borane (commonly known as BCF) catalyst has risen to prominence owing to its extensive versatility in the use of myriad of organic reactions. An efficient and highly stereoselective α-C-glycosylation strategy is presented by employing a catalytic amount of B(C₆F₅)₃ under mild reaction conditions en route to 2,3-unsaturated C-glycosides. The reaction features a broad functional group tolerance including a variety of glycals coupled with allyltrimethylsilane and trimethylsilylphenylacetylene to access the corresponding 2,3-unsaturated allyl- and alkynyl-C-glycosides with excellent α-selectivity. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor under mild conditions.

Key words

carbohydrate - glycal - tris(penta - fluorophenyl)borane - stereoselective - C-glycosylation - 2,3-unsaturated C-glycosides

Publication History

Received: 05 September 2023

Accepted after revision: 05 October 2023

Accepted Manuscript online:
05 October 2023

Article published online:
14 November 2023

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