<div class="csl-bib-body">
<div class="csl-entry">Rabong, C. V. (2007). <i>Scope and limitations of the t-reaction with emphasis on the synthesis of chiral heterocycles.</i> [Diploma Thesis, Technische Universität Wien]. reposiTUm. http://hdl.handle.net/20.500.12708/181924</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/181924
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dc.description.abstract
Employing a two-step sequence consisting of 1) nucleophilic aromatic substitution of ortho-Halo (Halogen=F, Cl) aromatic aldehydes or 1.1) Pd-catalyzed Buchwald-Hartwig aryl amination of ortho-Halo (Halo=Cl, Br) aromatic aldehydes with mostly (bi)cyclic secondary amines followed by 2) ring-closure via tert. amino effect (a sigmatropic [1,5]-hydride-shift) with C-H-acidic active methylene compounds as the key step, we obtained new heterocycles in mostly excellent yield and purity.<br />Further, we examined the stereoselectivity of the transformation in cases where it was deemed significant by means of single-crystal-X-Ray-diffraction (XRD) and correlated nuclear magnetic resonance spectroscopy (1H-1H- and 1H-13C - COSY-NMR); we used quantum mechanical calculations to support our reasoning, aswell.
de
dc.language
English
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dc.language.iso
en
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dc.subject
T-Reaktion
de
dc.subject
Heterozyklen
de
dc.subject
[1,5]-Wasserstoffumlagerung
de
dc.subject
Stereoselektivität
de
dc.subject
tert.-amino-effect
de
dc.subject
Spiro
de
dc.subject
Buchwald-Hartwig Arylaminierung
de
dc.subject
Pd-Kopplung
de
dc.subject
bizyklische Amine
de
dc.subject
Tandem
de
dc.subject
T-reaction
en
dc.subject
heterocycles
en
dc.subject
[1,5]-H-Shift
en
dc.subject
stereoselectivity
en
dc.subject
tert.-amino-effect
en
dc.subject
spiro
en
dc.subject
Buchwald-Hartwig Arylamination
en
dc.subject
Pd-coupling
en
dc.subject
bicyclic amines
en
dc.subject
tandem
en
dc.title
Scope and limitations of the t-reaction with emphasis on the synthesis of chiral heterocycles.
