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Diastereoselective Synthesis of C-Vinyl Glycosides via Gold(I)-Catalyzed Tandem 1,3-Acyloxy Migration/Ferrier Rearrangement
- Source :
- Organic letters. 20(1)
- Publication Year :
- 2017
-
Abstract
- A novel gold-catalyzed C-glycosylation has been developed to gain access to α,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate. This reaction involves a tandem intermolecular gold-catalyzed 1,3-acyloxy migration/Ferrier rearrangement with the involvement of allenic ester as the glycosyl acceptor. A wide range of substrate scope with good to excellent yields was achieved with complete diastereoselectivity. Ministry of Education (MOE) National Research Foundation (NRF) Accepted version We thank the Ministry of Education (MOE 2013-T3-1-002), National Research Foundation (NRF2016NRF-NSFC002-005), Nanyang Technological University, Singapore (RG14/16), China Scholarship Council (No. 201508420062), and Youth Talent Development Foundation of China Three Gorges University for their financial support. Dr. Yongxin Li and Dr. Ganguly Rakesh in the division of chemistry and biological chemistry, Nanyang Technological University are also acknowl-edged for X-ray analysis.
- Subjects :
- chemistry.chemical_classification
Ferrier rearrangement
Tandem
Catalysts
010405 organic chemistry
Stereochemistry
Organic Chemistry
Glycosyl acceptor
Chemical Reactions
Substrate (chemistry)
Glycoside
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
Chemistry [Science]
Carboxylate
Physical and Theoretical Chemistry
Subjects
Details
- ISSN :
- 15237052
- Volume :
- 20
- Issue :
- 1
- Database :
- OpenAIRE
- Journal :
- Organic letters
- Accession number :
- edsair.doi.dedup.....4ed41f0df77ac90841947a8f98b4a09a