Collect. Czech. Chem. Commun. 2000, 65, 539-548

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

Štěpán Vyskočila,*, Luděk Mecaa, Jiří Kubištab, Petr Maloňc and Pavel Kočovskýd,*

a Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, 182 23 Prague 8, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
d Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, U.K.


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.

Keywords: Biaryls; Binaphthyls; Chiral ligands; Chiral phosphines; Amine reductive alkylation; Chiral cavity; Circular dichroism; Enantioselective catalysis; N-Ligands; P-Ligands.

References: 51 live references.