Journal
ORGANIC LETTERS
Volume 20, Issue 13, Pages 4036-4039Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01602
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Funding
- DST-India [GAP-2155]
- DST-India under INSPIRE faculty programme [IFA-11-CH-18, GAP-1179]
- CSIR-New Delhi
- UGC-New Delhi
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The reaction of glycals containing good leaving groups with aromatic vinyl azides to give alpha-C-glycosyl amides in good yields is described. Various vinyl azides with different groups undergo the reaction smoothly. In these reactions, an iminodiazonium intermediate is generated by the attack of the vinyl azide onto the glycal under Lewis acid conditions. This undergoes Schmidt-type denitrogenative 1,2-migration to form a nitrilium ion, which, upon hydrolysis, gives the desired C-glycosyl amide.
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