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. 2020 Feb 24;59(9):3491-3494.
doi: 10.1002/anie.201914184. Epub 2020 Jan 29.

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

Yichu Liu  1   2   3 , Yibing Wang  2   3 , Wenhao Dai  2   3 , Wei Huang  2   3 , Yingxia Li  1 , Hong Liu  2   3
Affiliations

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

Yichu Liu et al. Angew Chem Int Ed Engl. .

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.

Keywords: C(sp3)−H activation; C-alkyl glycosides; diastereoselectivity; palladium; α-amino acids.

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