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Synthesis and asymmetric catalytic activity of (1S,1′S)-4,4′- biquinazoline-based primary amines

ArticleAçık Erişim

Özet

A series of (1S,1′S)-4,4′-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an (S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%. © 2011 Elsevier Ltd. All rights reserved.

Anahtar Kelimeler

1,1' (4,4' biquinazoline 2,2' diyl)bis(2 methylpropan 1 amine)1,1' (4,4' biquinazoline 2,2' diyl)bis(2 phenylethanamine)1,1' (4,4' biquinazoline 2,2' diyl)bis(2,2 dimethylpropan 1 amine)1,1' (4,4' biquinazoline 2,2' diyl)diethanaminealcoholaldehydeamineamino acidnickelunclassified drugarticlecatalysischlorinationdeprotection reactionenantiomerpolymerizationpriority journalsynthesis
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Tam Kayıt
AlanDeğerDil
dc.contributor.authorCakici, Murat
dc.contributor.authorCatir, Mustafa
dc.contributor.authorKarabuga, Semistan
dc.contributor.authorUlukanli, Sabri
dc.contributor.authorKilic, Hamdullah
dc.date.accessioned2026-10-18T20:30:33.414427515Z
dc.date.available2026-10-18T20:30:33.414427515Z
dc.date.issued2011
dc.description.abstractA series of (1S,1′S)-4,4′-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an (S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%. © 2011 Elsevier Ltd. All rights reserved.
dc.description.sponsorshipThe financial support from the Scientific and Technological Research Council of Turkey (TUBITAK) (TBAG-108T116) is gratefully acknowledged. In addition, the authors would like to thank Dr. Graham Eaton from Leicester University for the HRMS measurements.
dc.identifier.doi10.1016/j.tetasy.2011.01.009
dc.identifier.endpage308
dc.identifier.issn1362-511X
dc.identifier.issue3
dc.identifier.scopus2-s2.0-79953662680
dc.identifier.startpage300
dc.identifier.urihttps://rdlopen.rawdatalibrary.net/r/ebyu/15708
dc.identifier.volume22
dc.identifier.wosWOS:000290074800008
dc.language.isoen
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.relation.ispartofTetrahedron Asymmetry
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subject1,1' (4,4' biquinazoline 2,2' diyl)bis(2 methylpropan 1 amine)
dc.subject1,1' (4,4' biquinazoline 2,2' diyl)bis(2 phenylethanamine)
dc.subject1,1' (4,4' biquinazoline 2,2' diyl)bis(2,2 dimethylpropan 1 amine)
dc.subject1,1' (4,4' biquinazoline 2,2' diyl)diethanamine
dc.subjectalcohol
dc.subjectaldehyde
dc.subjectamine
dc.subjectamino acid
dc.subjectnickel
dc.subjectunclassified drug
dc.subjectarticle
dc.subjectcatalysis
dc.subjectchlorination
dc.subjectdeprotection reaction
dc.subjectenantiomer
dc.subjectpolymerization
dc.subjectpriority journal
dc.subjectsynthesis
dc.titleSynthesis and asymmetric catalytic activity of (1S,1′S)-4,4′- biquinazoline-based primary amines
dc.typeArticle
dspace.entity.typePublication
rdl.citation.scopus16
rdl.citation.wos15
rdl.source.indexSCOPUS
rdl.source.indexWOS
rdl.wos.indexScience Citation Index Expanded (SCI-EXPANDED)
rdl.wos.indexIndex Chemicus (IC)
rdl.wos.indexCurrent Chemical Reactions (CCR-EXPANDED)