Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 48, Pages 15884-15890Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403242
Keywords
acylation; enantioselectivity; kinetic resolution; mandelic acid esters; scandium
Categories
Funding
- National Natural Science Foundation of China [21321061, 21290182]
- Ministry of Education [20110181130014]
- National Basic Research Program of China (973 Program) [2010CB833300]
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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 acylat-ed 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.
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