Kinetically Controlled α‐Selective O‐Glycosylation of Phenol Derivatives Using 2‐Nitroglycals by a Bifunctional Chiral Thiourea Catalyst

Abstract

AbstractThe highly α‐selective organocatalytic glycosylation of phenol derivatives using 2‐nitroglycals has been developed. The stereoselectivity of this reaction was kinetically controlled by a bifunctional thiourea catalyst, the chirality of which was crucial for obtaining the high α‐selectivity. A variety of phenol derivatives were added to 2‐nitrogalactal with excellent stereoselectivity. The reaction of 2‐nitroglucal also achieved highly stereoselective glycosylation. The reaction was applied to the synthesis of glycopeptides.