Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids

Autor:	Józef Drabowicz, Anna Zawadzka, Jan K. Maurin, Joanna Szawkało, Andrzej Leniewski, Krystyna Wojtasiewicz, Stefan J. Czarnocki, Zbigniew Czarnocki
Rok vydání:	2007
Předmět:	Quinolizidine Tetrahydroisoquinoline Stereochemistry Organic Chemistry Enantioselective synthesis Iminium Transfer hydrogenation Catalysis Stereocenter Enamine Inorganic Chemistry chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Enantiomer
Zdroj:	Tetrahedron: Asymmetry. 18:406-413
ISSN:	0957-4166
Popis:	Four alkaloids: (R)-(+)-cryspine A 5, (R)-(+)-octahydroindolo[2,3-a]quinolizidine 8, (R)-(+)-harmicine 19 and (R)-(+)-desbromoarborescidine 22 were prepared via the asymmetric transfer hydrogenation reaction of a prochiral enamine (iminium salt). The enantiomeric excesses of the isolated alkaloids were determined from their 1H NMR spectra measured in the presence of (+)-(R)-tert-butylphenylphosphinothio(seleno)ic acids as chiral solvating agents. The absolute configurations at the newly created stereogenic carbon atoms were confirmed, in all cases, by X-ray crystallography.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9e8ed8b27191935ba6a18d521e7984c6 https://doi.org/10.1016/j.tetasy.2007.01.014 Zobrazit plný text záznamu Full Text from ScienceDirect