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Stereoselective Synthesis of C ‐Vinyl Glycosides via Palladium‐Catalyzed C−H Glycosylation of Alkenes
Author(s) -
Sun Qikai,
Zhang Huixing,
Wang Quanquan,
Qiao Tianjiao,
He Gang,
Chen Gong
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202104430
Subject(s) - stereoselectivity , chemistry , glycosylation , glycosyl , stereospecificity , glycoside , palladium , catalysis , organic chemistry , combinatorial chemistry , stereochemistry , biochemistry
C ‐vinyl glycosides are an important class of carbohydrates and pose a unique synthetic challenge. A new strategy has been developed for stereoselective synthesis of C ‐vinyl glycosides via Pd‐catalyzed directed C−H glycosylation of alkenes with glycosyl chloride donors using an easily removable bidentate auxiliary. Both the γ C−H bond of allylamines and the δ C−H bond of homoallyl amine substrates can be glycosylated in high efficiency and with excellent regio‐ and stereoselectivity. The resulting C ‐vinyl glycosides can be further converted to a variety of C ‐alkyl glycosides with high stereospecificity. These reactions offer a broadly applicable method to streamline the synthesis of complex C ‐vinyl glycosides from easily accessible starting materials.