Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 9, Pages 3491-3494Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914184
Keywords
alpha-amino acids; C(sp(3))-H activation; C-alkyl glycosides; diastereoselectivity; palladium
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Funding
- National Natural Science Foundation of China [21632008, 21672231, 21877118, 81773576, 81620108027]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDA12040107, XDA12040201]
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We have developed a highly efficient and practical approach for palladium-catalyzed trifluoroacetate-promoted N-quinolylcarboxamide-directed glycosylation of inert beta-C(sp(3))-H bonds of N-phthaloyl alpha-amino acids with glycals under mild conditions. For the first time, C(sp(3))-H activation for glycosylation was achieved to build C-alkyl glycosides. This method facilitates the synthesis of various beta-substituted C-alkyl glycoamino acids and offers a tool for glycopeptide synthesis.
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