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- Title
Conversion of Glycals to 2,3‐Di‐Substituted‐3‐Deoxy‐Glycals by N‐(Glycosyloxy) Acetamides‐assisted C‐2‐Alkenylation and C‐3‐Nucleophilic Substitution.
- Authors
Zargar, Irshad Ahmad; Hussain, Nazar; Mukherjee, Debaraj
- Abstract
Transformation of glycals to 2,3‐di‐substituted‐3‐dexoy‐glycals were achieved by sequential C2 alkenylation of pseudoglycals followed by capture of nucleophiles at C3 position. Anomeric linked N‐(glycosyloxy) acetamides group assisted innate C2‐H activation of pseudoglycals under palladium catalysis is achieved. The synthesized C2 alkenylated products were further attacked by thio/amino nucleophiles at C3 position under basic conditions in stereo‐selective fashion to generate 2,3‐branched glycals with the elimination of directing groups and translocation of double bond. Different control experiments were conducted to establish the role of directing groups in C−H functionalization of pseudoglycals and reason for selectivity.
- Subjects
GLYCALS; ACETAMIDE; DOUBLE bonds; ALKENYLATION; NUCLEOPHILES; PALLADIUM
- Publication
Chemistry - An Asian Journal, 2022, Vol 17, Issue 14, p1
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.202200350