Palladium-Catalysed C(sp3 )-H Glycosylation for the Synthesis of C-Alkyl Glycoamino Acids.

Abstract

We have developed a highly efficient and practical approach for palladium-catalyzed trifluoroacetate-promoted N-quinolylcarboxamide-directed glycosylation of inert β-C(sp3 )-H bonds of N-phthaloyl α-amino acids with glycals under mild conditions. For the first time, C(sp3 )-H activation for glycosylation was achieved to build C-alkyl glycosides. This method facilitates the synthesis of various β-substituted C-alkyl glycoamino acids and offers a tool for glycopeptide synthesis.