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Chiral Brønsted Acid Mediated Glycosylation with Recognition of Alcohol Chirality
Author(s) -
Kimura Tomoya,
Sekine Maiko,
Takahashi Daisuke,
Toshima Kazunobu
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201304830
Subject(s) - chemistry , glycosylation , chirality (physics) , glycoside , enantiomer , alcohol , phosphoric acid , yield (engineering) , sugar , stereochemistry , organic chemistry , biochemistry , chiral symmetry , materials science , physics , quantum mechanics , nambu–jona lasinio model , quark , metallurgy
Sugar sugar : In the glycosylation of racemic alcohols with 1 using the chiral phosphoric acid 2 as an activator, one enantiomer of the racemic alcohol selectively reacts with 1 to give the corresponding glycoside with good to excellent α/β‐stereo‐ and diastereoselectivity in high yield. The reaction was successfully applied to the synthesis of a chiral natural flavan glycoside using a racemic aglycon.