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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

Author(s)
Some, SurajitBae, Han YongKim, Mun JongZhang, Yong JianSong, Choong Eui
Issued Date
2017-08
DOI
10.1002/ejoc.201700786
URI
https://scholarworks.unist.ac.kr/handle/201301/25868
Fulltext
https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201700786
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).
Publisher
WILEY-V C H VERLAG GMBH
ISSN
1434-193X
Keyword (Author)
Ultrasound irradiationBronsted base catalysisDecarboxylationAmino acidsEnantioselectivityChiral cinchona-based squaramides
Keyword
MICHAEL-ADDITIONASYMMETRIC-SYNTHESISBETA-NITROOLEFINSACIDSORGANOCATALYSTSDERIVATIVESNITROALKENESRECOGNITIONCATALYSISCENTERS

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