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Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation

URN to cite this document: urn:nbn:de:bvb:355-opus-2846

Baur, Markus A. (2003) Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation. PhD, Universität Regensburg

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Abstract (German)

Die Methode der enantioselektiven Decarboxylierung wurde angewendet, um Enantiomeren-angereicherte alpha-Aminosäurederivate und alpha-Fluorketone zu erhalten. Als Substrate wurden 2-N-Acetylamino-2-alkylmalonsäuremonoethylester beziehungsweise beta-Keto-benzylester verwendet. China-Alkaloide und Derivate davon wurden als Katalysatoren eingesetzt. Die besten erhaltenen Ergebnisse waren N-Acetyl-L-phenylalaninethylester mit 70% Enantiomerenüberschuß unter Verwendung der katalytisch aktiven Base N-(9-Deoxyepicinchonin-9-yl)-4-methoxybenzamid und 2-Fluor-1-tetralon mit 65% Enantiomerenüberschuß mit Chinin als Katalysator.

Translation of the abstract (English)

The method of enantioselective decarboxylation was applied to obtain enantioenriched alpha-amino acid derivatives and alpha-fluoro ketones. 2-N-acetylamino-2-alkylmalonic monoethylesters respectively benzyl beta-ketoesters were applied as substrates. Cinchona alkaloids and derivatives of them were used as catalysts. The best results obtained were ethyl N-acetyl-L-phenylalaninate with 70% enantiomeric excess using the catalytically active base N-(9-deoxyepicinchonine-9-yl)-4-methoxybenzamide and 2-fluoro-1-tetralone with 65% enantiomeric excess with the catalyst quinine.

Item Type:	Thesis of the University of Regensburg (PhD)
Referee:	Henri (Prof. Dr.) Brunner
Date of exam:	15 July 2003
Institutions:	Chemistry and Pharmacy > Institut für Anorganische Chemie > Emeriti > Prof. Dr. Henri Brunner
Keywords:	Asymmetrische Synthese / Katalyse , Aminosäurederivate , Decarboxylierung , alpha-Fluorketone , China-Alkaloidderivate , Asymmetric catalysis , alpha-amino acid derivatives , alpha-fluoroketones , decarboxylation , cinchona alkaloid derivatives
Subjects:	500 Science > 540 Chemistry & allied sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Yes
Owner:	Universitätsbibliothek Regensburg
Deposited On:	26 Oct 2009 14:09
Last Modified:	12 Nov 2012 13:04
Item ID:	10117

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