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

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Title: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
Creators:
Vyskočil, Štěpán
Meca, Luděk
Kubišta, Jiří
Maloň, Petr
Kočovský, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 4, pp. 539-548
Uncontrolled Keywords:Chiral phosphines, Biaryls, <i>P</i>-Ligands, Binaphthyls, <i>N</i>-Ligands, Circular dichroism, Chiral cavity, Enantioselective catalysis, Chiral ligands, Amine reductive alkylation

Abstract

Reductive amination of 2-hydroxybenzaldehyde, using a combination of NaBH<sub>4</sub> and (<i>R</i>)-[1,1'-binaphthalene]-2,2'-diamine, served as the key step in the synthesis of the potentially tetradentate ligands (<i>R</i>)-<i>N</i>,<i>N'</i>-bis(2-hydroxybenzyl)[1,1'-binaphthalene]-2,2'-diamine and (<i>R</i>)-<i>N</i>,<i>N'</i>-bis(2-hydroxybenzyl)-<i>N</i>,<i>N'</i>-dimethyl[1,1'-binaphthalene]-2,2'-diamine. In analogy, amination of 2-bromobenzaldehyde with (<i>R</i>)-[1,1'-binaphthalene]-2,2'-diamine produced (<i>R</i>)-<i>N</i>,<i>N'</i>-bis(2-bromobenzyl)[1,1'-binaphthalene]-2,2'-diamine, whose conversion into the novel diphosphine ligand (<i>R</i>)-<i>N</i>,<i>N'</i>-bis[2-(diphenylphosphino)benzyl]-<i>N</i>,<i>N'</i>-dimethyl- [1,1'-binaphthalene]-2,2'-diamine was readily attained in two steps. CD spectra of the new binaphthyl derivatives are presented. <p>

Title: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
Creators:
Vyskočil, Štěpán
Meca, Luděk
Kubišta, Jiří
Maloň, Petr
Kočovský, Pavel
Uncontrolled Keywords:Chiral phosphines, Biaryls, <i>P</i>-Ligands, Binaphthyls, <i>N</i>-Ligands, Circular dichroism, Chiral cavity, Enantioselective catalysis, Chiral ligands, Amine reductive alkylation
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:4
Page Range:pp. 539-548
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000539UNSPECIFIED
ID Code:1659
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Vyskočil, Štěpán; Meca, Luděk; Kubišta, Jiří; Maloň, Petr; Kočovský, Pavel (2000) 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. Collection of Czechoslovak Chemical Communications, 65 (4). pp. 539-548. ISSN 0010-0765

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