Stereoselective effects in the solid-phase hydrogenation of unsaturatedl-hydroxyproline derivatives

Autor:	Yu. A. Zolotarev, E. M. Dorokhova, E. V. Laskatelev, N. F. Myasoedov, Yu. A. Borisov, S. G. Rozenberg, V. S. Kozik
Rok vydání:	1997
Předmět:	chemistry.chemical_classification Allylic rearrangement Crystallography chemistry Isotope Stereochemistry Phase (matter) Atom Molecule Stereoselectivity General Chemistry Hydrogen spillover Amino acid
Zdroj:	Russian Chemical Bulletin. 46:1726-1729
ISSN:	1573-9171 1066-5285
DOI:	10.1007/bf02495124
Popis:	The solid-phase catalytic hydrogenation of (R-4tert-butoxy-Δ1-pyrroline-2-carboxylic) acid under the action of hydrogen spillover was studied. The reaction proceeds stereoselectively with the predominant formation of thel-amino acid. The configuration of the asymmetric center formed is determined by that of the asymmetric C(4) atom. The major portion of the isotope label is incorporated into the allylic C(3) and C(5) positions, and the β-H atoms are more mobile. Using quantum-chemical calculations, the geometric structure of thel-hydroxyproline molecule was calculated, and the spin-spin coupling constants for this tritium-labeled amino acid were determined.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d532304e5190732e6ad0d7795fc12daa https://doi.org/10.1007/bf02495124 Zobrazit plný text záznamu Full text from SpringerLink