A Facile Synthesis of the Enantiopure, Nitrogen-Substituted 2,2'-Diamino-1,1'-binaphthyls as Potential Ligands for Catalytic Asymmetric Reactions

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Title:A Facile Synthesis of the Enantiopure, Nitrogen-Substituted 2,2'-Diamino-1,1'-binaphthyls as Potential Ligands for Catalytic Asymmetric Reactions
Creators:
Vyskočil, Štěpán
Smrčina, Martin
Kočovský, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 4, pp. 515-519
Uncontrolled Keywords:Biaryls, Amine arylation, Binaphthyls, Palladium catalysis, Chiral ligands, Amine reductive alkylation, Axial chirality

Abstract

Reductive alkylation of (<i>R</i>)-(+)-2,2'-diamino-1,1'-binaphthyl (<strong>1</strong>) with various ketones has been accomplished by means of NaBH<sub>4</sub>/H<sub>2</sub>SO<sub>4</sub> in THF at room temperature. Bisalkylation predominated with the sterically less demanding acetone (<strong>1→3a</strong>; 82%), whereas the bulky 2-adamantanone afforded mainly the monoalkylated product <strong>4c</strong> (71%). Both mono- and bisalkylated diamines (<i>R</i>)-<strong>3</strong> and (<i>R</i>)-<strong>4</strong> were reductively permethylated on reaction with CH<sub>2</sub>O, NaBH<sub>4</sub>, and H<sub>2</sub>SO<sub>4</sub>. The Pd(0)-catalyzed phenylation of (<i>R</i>)-(+)-<strong>1</strong> with PhBr afforded the <i>N</i>,<i>N</i>'-diphenyl derivative (<i>R</i>)-<strong>7</strong> (70%).

Title:A Facile Synthesis of the Enantiopure, Nitrogen-Substituted 2,2'-Diamino-1,1'-binaphthyls as Potential Ligands for Catalytic Asymmetric Reactions
Creators:
Vyskočil, Štěpán
Smrčina, Martin
Kočovský, Pavel
Uncontrolled Keywords:Biaryls, Amine arylation, Binaphthyls, Palladium catalysis, Chiral ligands, Amine reductive alkylation, Axial chirality
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:63
Number:4
Page Range:pp. 515-519
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980515UNSPECIFIED
ID Code:1316
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Vyskočil, Štěpán; Smrčina, Martin; Kočovský, Pavel (1998) A Facile Synthesis of the Enantiopure, Nitrogen-Substituted 2,2'-Diamino-1,1'-binaphthyls as Potential Ligands for Catalytic Asymmetric Reactions. Collection of Czechoslovak Chemical Communications, 63 (4). pp. 515-519. ISSN 0010-0765

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