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Kinetic Resolution of Racemic Mandelic Acid Esters by N , N′ ‐Dioxide–Scandium‐Complex‐Catalyzed Enantiomer‐Selective Acylation
Author(s) -
Zhang Yuheng,
Liu Xiaohua,
Zhou Lin,
Wu Wangbin,
Huang Tianyu,
Liao Yuting,
Lin Lili,
Feng Xiaoming
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403242
Subject(s) - kinetic resolution , mandelic acid , chemistry , acylation , enantioselective synthesis , yield (engineering) , catalysis , scandium , enantiomer , enantiomeric excess , organic chemistry , selectivity , medicinal chemistry , materials science , metallurgy
A simple and efficient acylative kinetic resolution of racemic mandelic acid esters was accomplished with a chiral N , N ’‐dioxide–scandium(III) complex under mild and base‐free reaction conditions. A variety of mandelic acid esters performed well in the reaction, obtaining both acylated products (up to 49% yield, 97% ee ) and recovered substrates (up to 49% yield, 95% ee ) in high enantioselectivities with perfect selectivity factors (up to 247). The enantioselective recognition and catalytic models were also proposed for the catalytic KR reaction.