Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 36, Pages 19620-19625Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202104430
Keywords
alkene functionalization; auxiliary; C-H glycosylation; C-vinyl glycoside; palladium
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Funding
- 111 project of MOE China [B06005]
- [NSFC-21725204]
- [NSFC-22071119]
- [NCC2020FH02]
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A new strategy has been developed for the stereoselective synthesis of C-vinyl glycosides, using Pd-catalyzed directed C-H glycosylation. This method offers a broadly applicable approach to streamline the synthesis of complex C-vinyl glycosides with high efficiency and excellent regio- and stereoselectivity.
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 gamma C-H bond of allylamines and the delta 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.
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