60652-04-2Relevant academic research and scientific papers
Synthesis of conformationally restricted glutamate and glutamine derivatives from carbonylation of orthopalladated phenylglycine derivatives
Urriolabeitia, Esteban P.,Laga, Eduardo,Cativiela, Carlos
, p. 1569 - 1575,7 (2020/09/14)
A new method for the regioselective synthesis of 2-alkoxycarbonyl- and 2-(aminocarbonyl)phenylglycinate methyl esters has been developed. The reaction of the orthopalladated complex [Pd(μ-Cl)(C6H 4(CH(CO2Me)NMe2)-2)]2 (1) with nucleophiles HNu under a CO atmosphere results in the selective incorporation of the C(O)Nu moiety to the phenyl ring and formation of the carbonyl species ortho-C6H4(C(O)Nu)(CH(CO2Me)NMe2) (2a-j) (Nu = OR, NHR, NR2). Compounds 2a-j are conformationally restricted analogues of glutamic acid and glutamine and are interesting due to their biological and pharmacological properties. The reaction of [Pd(μ-Cl)(C6H4(CH(CO2Me)NHTf)-2)] 2 (3) with nucleophiles in a CO atmosphere results, however, in the formation of the cyclic isoindolinone or the open 2-carboxyphenylglycine methyl esters, with the reaction outcome being driven by the choice of the solvent.
Metal complexes of biologically important ligands, CIV [1]. Ortho-palladated complexes of N,N-dimethyl-C-phenylglycine-methylester. Synthesis of α-amino acid derivatives by insertion of isocyanides, CO, alkenes, and alkynes into the Pd-C bond
B?hm, Andreas,Polborn, Kurt,Sünkel, Karlheinz,Beck, Wolfgang
, p. 448 - 458 (2007/10/03)
N,N-Dimethyl-C-phenylglycinemethylester reacts with Pd(OAc)2 in acetic acid to give the orthopalladated, acetato bridged complex 1. Treatment of 1 with sodium halide affords the chloro, bromo, and iodo bridged compounds [Me2NC(H)(CO2Me)C6H4PdX]2 (2a - c) (X = halide). From 2a and 1,1′-bis(diphenylphosphino)ferrocene the phosphine bridged trinuclear complex 3 is obtained. Substitution of the amine ligand of 2a by the phosphino group is observed for the reaction of 2a with Ph2PC(Me)C(Me)PPh2. Insertion of 2,6-dimethyl-phenylisocyanide, CO, alkyl-vinyl-ketones, and diphenylacetylene into the Pd-C bond of 2a - c provides the ortho-substituted organic and organometallic derivatives of phenylglycine 6a - c, 7, 8a - b and 9a - c. The crystal structures of 1, 4a, 6a, 7 and 9a were determined by X-ray diffraction.
