111900-32-4Relevant articles and documents
Stephani et al.
, p. 4094,4096 (1972)
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.
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
