Enantioselective synthesis of (S)-4-methyleneglutamic acid via tandem conjugate addition-elimination under phase-transfer catalytic conditions

Title
Enantioselective synthesis of (S)-4-methyleneglutamic acid via tandem conjugate addition-elimination under phase-transfer catalytic conditions
Author(s)
강석훈[강석훈]Qinghua Shi[Qinghua Shi]하민우[하민우]구진모[구진모]Maosheng Cheng[Maosheng Cheng]정병선박형근[박형근]주상섭[주상섭]
Keywords
ALPHA-AMINO-ACIDS; GLUTAMIC-ACID; ALKYLATION; DERIVATIVES; PLANTS
Issue Date
201006
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
TETRAHEDRON, v.66, no.24, pp.4326 - 4329
Abstract
An efficient enantioselective synthetic method for (S)-4-methyleneglutamic acid is reported. Phase-transfer catalytic conjugate addition elimination of the benzophenone imine of glycine tert-butyl ester in the presence of chiral Cinchona-derived catalysts give the corresponding conjugated addition products (>99% ee), which could be hydrolyzed to chiral (S)-4-methyleneglutamic acid. (C) 2010 Elsevier Ltd. All rights reserved.
URI
http://hdl.handle.net/YU.REPOSITORY/22338http://dx.doi.org/10.1016/j.tet.2010.04.034
ISSN
0040-4020
Appears in Collections:
약학대학 > 약학부 > Articles
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