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- W1978461180 abstract "Es wird die interne asymmetrische Synthese von (-)-( lR,3R)-trans-3-Methylcyclohexanamin-hydrochlorid (4) und 3a-Aminocholestan (9) durch reduktive Aminierung mit racem. 1-Phenylethylamin in einem Dreistufenverfahren beschrieben. Die aus den Ketonen 1 und 6 durch Kondensation mit 1-Phenyl-ethylaminen als chiralen Hilfsaminen leicht zugänglichen Imine 2 und 7 werden mit Raney-Nickel zu den sekundaren Aminen 3a-f und 8d-f hydriert. Hydrogenolyse über Pd-Katalysator führt zu den primaren Aminen 4 und 9. Die Enantionmerenreinheit von (-)-(1R,3R)-4 wird über die diastereomeren Acylamine 5 durch HPLC bestimmt. Die Konfiguration der Verbindungen 3 und 4 sowie 8 und 9 wird durch H- und 3C-NMR-Spektroskopie ermittelt. Asymmetric Reductive Amination of Cycloalkanones, IV: Synthesis of Optically Active tms-3-Substituted Cyclohexanamines Internal asymmetric syntheses of (-)-( 1R,3R)-trans-3-methylcyclohexanaminium chloride (4) and cholestan-3a-amine (9) by means of reductive amination with racem. 1-phenylethylamine in a three-step procedure are described. Condensations of the ketones 1 and 6 with 1-phenylethylamines as auxiliary chiral amines lead to the imines 2 and 7, which are hydrogenated to the secondary amines 3s-f and 8d-f with Raney nickel. Hydrogenolyses with Pd yield the primary amines 4 and 9. Enantiomeric excess of (-)-( 1R,3R)-4 is determined via the diastereomeric acylamines 5 by means of HPLC. Stereochemical analysis of 3, 4, 8 and 9 is performed hy H- and I3C-NMR spectroscopy." @default.
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- W1978461180 date "1985-01-01" @default.
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- W1978461180 title "Asymmetrische reduktive Aminierung von Cycloalkanonen, 4. Mitt. Synthese optisch aktiver trans-3-substituierter Cyclohexanamine" @default.
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- W1978461180 doi "https://doi.org/10.1002/ardp.19853180611" @default.
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