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- W2015668465 abstract "Es wird die EPC-Synthese (Enantiomerically Pure Compounds) der optisch aktiven cis-bicyclischen Lactame 5 mit annellierten 5.5-, 5.6-, 6.5- und 6.6- gliedrigen Ringen sowie der korrespondierenden optisch aktiven cis-bicyclischen Amin-Hydrochloride 6 (Cyclopentanopyrrolidin, Octahydroperindin, Perhydroindol und Dekahydrochinolin) aus den kongeneren cycloaliphatischen Aminosäureestern 4 durch intramolekulare Aminolyse und nachfolgende Lithiumalanat-Reduktion beschrieben. Die erforderlichen Ausgangsverbindungen 4 werden aus den racemischen Cycloalkanon-2-essig- bzw. 2-propionsäureestern 1 und den chiralen Hilfsaminen R-(+)- bzw. S-(−)-1-Phenylethylamin durch dreistufige asymmetrische Synthesen gewonnen1). Die relative Konfiguration der Verbindungen 5 und 6 wurde durch 1H-NMR-Spektroskopie, die optische Reinheit der optisch aktiven cis-bicyclischen Amin-Hydrochloride 6 durch HPLC der entspr. Mosher-Amide 7 bestimmt. Asymmetric Reductive Amination of Cycloalkanones, X: EPC-Synthesis of cis-Bicyclic Lactames and Amines We report the EPC-synthesis (Enantiomerically Pure Compounds) of optically active cis-bicyclic lactames 5 with annellated 5.5-, 5.6-, 6.5- and 6.6- membered rings, as well as their corresponding optically active cis-bicyclic amine hydrochlorides 6: cyclopentanopyrrolidine, octa-hydropyrindine, perhydroindole and decahydroquinoline by intramolecular aminolysis of the corresponding primary 1-aminocycloalkane-2-acetic and 2-propionic acid ester hydrochlorides 4 and subsequent lithiumalanate-reduction. The starting compounds 4 are synthesised in an asymmetric three-step-procedure from the cycloalkanone-2-acetic and 2-propionic acid ethyl esters 1 and the chiral auxiliary R-(+)- and S-(−)-1-phenylethylamine. The relative configurations of compounds 5 and 6 were derived from 1H-NMR-spectroscopy. The optical purity of the optically active cis-bicyclic amine hydrochlorides 6 is determined by HPLC-analysis of the corresponding Mosher-amides 7." @default.
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- W2015668465 title "Asymmetrische reduktive Aminierung von Cycloalkanonen, 10. Mitt.: EPC-Synthesecis-bicyclischer Lactame und Amine" @default.
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- W2015668465 doi "https://doi.org/10.1002/ardp.19903231109" @default.
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