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Bae, Han Yong
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Ultrasound-Promoted Enantioselective Decarboxylative Protonation of alpha-Aminomalonate Hemiesters by Chiral Squaramides: A Practical Approach to Both Enantiomers of alpha-Amino Esters

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Title
Ultrasound-Promoted Enantioselective Decarboxylative Protonation of alpha-Aminomalonate Hemiesters by Chiral Squaramides: A Practical Approach to Both Enantiomers of alpha-Amino Esters
Author
Some, SurajitBae, Han YongKim, Mun JongZhang, Yong JianSong, Choong Eui
Keywords
Ultrasound irradiation;  Bronsted base catalysis;  Decarboxylation;  Amino acids;  Enantioselectivity;  Chiral cinchona-based squaramides
Issue Date
201708
Publisher
WILEY-V C H VERLAG GMBH
Citation
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v.2017, no.31, pp.4562 - 4565
Abstract
Herein, we report an ultrasound-promoted enantio-selective decarboxylative protonation reaction of alpha-aminomalonate hemiesters 1 in the presence of chiral cinchona-derived squaramide Bronsted bases under mild conditions, which afforded both the (S)- and (R)-enantiomers of alpha-amino acid derivatives 2 in excellent yields (>90 %) and excellent enantioselectivities (up to 98 % ee).
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DOI
http://dx.doi.org/10.1002/ejoc.201700786
ISSN
1434-193X
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