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Tris(Pentafluorophenyl)Borane‐Driven Stereoselective O ‐Glycosylation with Glycal Donors under Mild Condition
Author(s) -
Bihari Mishra Kunj,
Kandasamy Jeyakumar
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900055
Subject(s) - glycal , chemistry , borane , glycosylation , stereoselectivity , yield (engineering) , tris , glycoside , sugar , organic chemistry , medicinal chemistry , stereochemistry , catalysis , biochemistry , materials science , metallurgy
Activation of glycal donors was achieved using tris(pentafluorophenyl)borane [B(C 6 F 5 ) 3 ] under mild reaction conditions. The glycosylation reaction proceeded efficiently with a wide range of sugar and non‐sugar acceptors and provided α‐selective glycosides in high yield. Interestingly, under different reaction conditions, Ferrier rearrangement products or 2‐deoxyglycosides (i. e. addition products) were obtained as major products with benzyl‐protected glycal donors.