477331-06-9Relevant academic research and scientific papers
Stereoselective synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid via C-H insertion of alkylidenecarbene.
Ohira, Susumu,Akiyama, Megumi,Kamihara, Kumiko,Isoda, Yuichi,Kuboki, Atsuhito
, p. 887 - 891 (2002)
(1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic acid (ACPD), a potent agonist of metabotropic glutamate receptors, was synthesized from L-serine. The chiral quaternary center was constructed by C-H insertion of the alkylidenecarbene, this being generated by the reaction between lithiotrimethylsilyldiazomethane and the corresponding ketone.
Enantioselective synthesis of the excitatory amino acid (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid
Bradley, Daniel M.,Mapitse, Renameditswe,Thomson, Nicholas M.,Hayes, Christopher J.
, p. 7613 - 7617 (2007/10/03)
An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed.
Carbamate-directed hydroboration: Enantioselective synthesis of the excitatory amino acid 1-aminocyclopentane-1,3-dicarboxylic acid
Hodgson, David M.,Thompson, Alison J.,Wadman, Sjoerd
, p. 3357 - 3358 (2007/10/03)
Carbamate-directed hydroboration (using BH3) of 1-substituted 3- cyclopentenes 2, 6 and 9 and an enantioselective synthesis of the excitatory amine acid 1-aminocyclopentane-1,3-dicarboxylic acid via carbamate-directed asymmetric hydroboration [90% de, 45% ee using (+)-IpcBH2] of cyclopentene 2 are described.
Stereospecific synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid, a selective agonist of metabotropic glutamate receptors
Ma, Dawei,Ma, Jingyuan,Dai, Lixin
, p. 825 - 827 (2007/10/03)
(1S,3R)-Aminocyclopentane-1,3-dicarboxylic acid 1, a widely used metabotropic glutamate receptor agonist has been synthesized. Hydrolysis followed by Curtius rearrangement of 5 derived from dimethyl (S)-malate gave 6 with excellent diastereofacial selecti
Resolution and regioselective protection of glutamic acid analogues. I- Resolution of diastereomeric α-boroxazolidone derivatives
Acher,Azerad
, p. 731 - 744 (2007/10/02)
Diastereomeric α-boroxazolidone γ-phenylethylamide (or γ-phenylethanolamide) derivatives of 2-, 3- or 4-substituted glutamic acid analogues have been separated by silicagel chromatography, resulting, after deprotection, in a practical method for the resolution of most of these unnatural amino acids.
CHEMOENZYMATIC SYNTHESIS OF CONFORMATIONALLY RIGID GLUTAMIC ACID ANALOGUES
Trigalo, F.,Buisson, D.,Azerad, R.
, p. 6109 - 6112 (2007/10/02)
All stereomers of cyclohexane cyclopentane-derived analogues of glutamic acid have been synthesized from the corresponding 3-keto-cycloalkyl carboxylic acid esters by a combination of microbial steps and standard chemical methods.
