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Synthesis and characterization of N-substituted (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides as organocatalysts for asymmetric aldol reaction
Authors: Androvič Ladislav | Drabina Pavel | Panov Illia | Harmand Lydie | Padělková Zdeňka | Sedlák Miloš
Year: 2014
Type of publication: článek v odborném periodiku
Name of source: Heterocycles
Publisher name: The Japan Institute of Heterocyclic Chemistry
Place: Tokyo
Page from-to: 1844-1859
Titles:
Language Name Abstract Keywords
cze Syntéza a charakterizace N-substituovaných (S)-1,2,3,4-tetrahydroisochinolin-3-karboxamidů a thioamidů jako organokatalyzátoru pro asymetrickou aldolovou reakci V této práci byla popsána příprava a charakterizace osmi opticky čistých N-substituovaných (S)-1,2,3,4-tetrahydroisochinolin-3-karboxamidů a thioamidů. Připravené amidy a thioamidy byly testovány jako organokatalyzátory pro aldolizaci 4-nitrobenzaldehydu a acetonu. Nejvyššího enantiomerního přebytku u vznikajicího 4-hydroxy-4-(4-nitrofenyl)butan-2-onu bylo dosaženo s (S)-N-[(1R)-1-fenylethyl]-1,2,3,4-tetrahydroisochinolin-3-thiokarboxamidem (77% ee). Sníženou katalytickou aktivitu těchto katalyzátorů ve srovnání s (S)-prolinovými deriváty lze vysvětlit vznikem málo reaktivního cyklického intermediátu, který byl izolován a charakterizován. 1,2,3,4-tetrahydroisochinolin-3-karboxamid; organokatalýza; asymetrická aldolizace
eng Synthesis and characterization of N-substituted (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides as organocatalysts for asymmetric aldol reaction In this paper, the preparation and characterization of eight optically pure N-functionalized (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxamides and thioamides is described. The prepared amides and thioamides were tested as organocatalysts of aldol reaction of 4-nitrobenzaldehyde and acetone. The highest ee of formation of 4-hydroxy-4-(4-nitrophenyl)butan-2-one was obtained with (S)-N-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide (77% ee). The observed deceleration of the aldol reaction catalyzed in this way, as compared with that catalyzed with (S)-proline, was attributed to the formation of little reactive cyclic intermediate, which was isolated and characterized. 1,2,3,4-tetrahydroisoquinoline-3-carboxamide; organocatalysts; asymmetric aldolization

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