Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides

摘要

A practical approach for the ∝-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocataly-sis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors and its versatility is exempli-fied in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chi-ral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.