Synthesis of C2-Symmetrical [1,1'-Binaphthalene]-2,2'-diamines with Additional Chelating Groups Attached to the Nitrogen Atoms as Potential Ligands for Asymmetric Catalysis

Autor:	Jiří Kubišta, Luděk Meca, Štěpán Vyskočil, Pavel Kočovský, Petr Maloň
Rok vydání:	2000
Předmět:	Circular dichroism Chemistry Ligand Stereochemistry Enantioselective synthesis chemistry.chemical_element General Chemistry Reductive amination Medicinal chemistry Nitrogen chemistry.chemical_compound Diamine Chelation Amination
Zdroj:	Collection of Czechoslovak Chemical Communications. 65:539-548
ISSN:	1212-6950 0010-0765
DOI:	10.1135/cccc20000539
Popis:	Reductive amination of 2-hydroxybenzaldehyde, using a combination of NaBH4 and (R)-[1,1'-binaphthalene]-2,2'-diamine, served as the key step in the synthesis of the potentially tetradentate ligands (R)-N,N'-bis(2-hydroxybenzyl)[1,1'-binaphthalene]-2,2'-diamine and (R)-N,N'-bis(2-hydroxybenzyl)-N,N'-dimethyl[1,1'-binaphthalene]-2,2'-diamine. In analogy, amination of 2-bromobenzaldehyde with (R)-[1,1'-binaphthalene]-2,2'-diamine produced (R)-N,N'-bis(2-bromobenzyl)[1,1'-binaphthalene]-2,2'-diamine, whose conversion into the novel diphosphine ligand (R)-N,N'-bis[2-(diphenylphosphino)benzyl]-N,N'-dimethyl- [1,1'-binaphthalene]-2,2'-diamine was readily attained in two steps. CD spectra of the new binaphthyl derivatives are presented.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::922beee8dd7df8480c49ae807aeced63 https://doi.org/10.1135/cccc20000539 Zobrazit plný text záznamu