Ultrasound-Promoted Enantioselective Decarboxylative Protonation of [alpha]-Aminomalonate Hemiesters by Chiral Squaramides: A Practical Approach to Both Enantiomers of [alpha]-Amino Esters

Herein, we report an ultrasound-promoted enantioselective decarboxylative protonation reaction of [alpha]-aminomalonate hemiesters 1 in the presence of chiral cinchona-derived squaramide Brønsted bases under mild conditions, which afforded both the (S)- and (R)-enantiomers of [alpha]-amino acid deri...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-08, Vol.2017 (31), p.4562
Main Authors: Some, Surajit, Kim, Han Yong Bae, Mun Jong, Zhang, Yong Jian, Song, Choong Eui
Format: Article
Language:English
Subjects:
Enantiomers
Esters
Protonation
Ultrasonic imaging
Online Access:Get full text
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Summary:Herein, we report an ultrasound-promoted enantioselective decarboxylative protonation reaction of [alpha]-aminomalonate hemiesters 1 in the presence of chiral cinchona-derived squaramide Brønsted 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).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700786