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Silicon Fluorides for Acid‐Base Catalysis in Glycosidations
Author(s) -
Kumar Amit,
Geng Yiqun,
Schmidt Richard R.
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100933
Subject(s) - chemistry , glycosyl , glycosyl donor , anomer , nucleophile , catalysis , intramolecular force , selectivity , acceptor , nucleophilic substitution , base (topology) , adduct , lewis acids and bases , medicinal chemistry , nucleophilic aromatic substitution , organic chemistry , stereochemistry , mathematical analysis , physics , mathematics , condensed matter physics
Adduct formation between alcohols as glycosyl acceptors and phenylsilicon trifluoride (PhSiF 3 ) as catalyst permits acid‐base‐atalyzed glycosidations with O ‐glycosyl trichloroacetimidates as glycosyl donors. In this way, from various glycosyl donors and acceptors 1,2‐ trans‐ and some 1,2‐ cis ‐glycosides could be obtained with high anomeric selectivity. A preference for an intramolecular bimolecular nucleophilic substitution (S N 2‐type) reaction course with concomitant donor and acceptor activation is supported by the results.