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The synthesis and characterisation of N-(1-carbamoyl-1,1-dialkyl-methyl)-(S)-prolinamides and related pyrrolidin-2-yl-4,5-dihydro-1H-imidazol-5-ones as potential enantioselective organocatalysts
Authors: Panov Illia | Drabina Pavel | Hanusek Jiří | Sedlák Miloš
Year: 2011
Type of publication: článek v odborném periodiku
Name of source: Tetrahedron Asymmetry
Publisher name: Elsevier Science BV
Place: Amsterdam
Page from-to: 215-221
Titles:
Language Name Abstract Keywords
cze Syntéza a charakterizce N-(1-karbamoyl-1,1-dialkyl-methyl)-(S)-prolinamidů a příbuzných pyrrolidin-2-yl-4,5-dihydro-1H-imidazol-5-onů jako potenciálních enantioselectivních organokatalyzátorů Acylace substituovaných 2-aminopropanamidů (2S)-Boc-prolinem, (2S)-Cbz-prolinem a (2S)-Bn-prolinem byla použita k přípravě substituovaných 1-chráněných N-(1-karbamoyl-1,1-dialkyl-methyl)-(S)-prolinamidů (74-89%), jejichž následnou deprotekcí byly získány N-(1-karbamoyl-1,1-dialkyl-methyl)-(S)-prolinamidy (94-95%). Získané enantiomerně čisté N-(1-karbamoyl-1,1-dialkyl-methyl)-(S)-prolinamidy byly testovány jako organokatalyzátory aldolové reakce cyklohexanonu s 4-nitrobenzaldehydem, s výtěžky od 38% do 79% ee. L-prolin, organokatalýza;2-aminopropanamidy
eng The synthesis and characterisation of N-(1-carbamoyl-1,1-dialkyl-methyl)-(S)-prolinamides and related pyrrolidin-2-yl-4,5-dihydro-1H-imidazol-5-ones as potential enantioselective organocatalysts The acylation of substituted 2-aminopropanamides with (2S)-Boc-proline, (2S)-Cbz-proline and (2S)-Bn-proline was used to prepare substituted 1-protected N-(1-carbamoyl-1,1-dialkyl-methyl)-(S)-prolinamides (74-89%), whose subsequent deprotection gave N-(1-carbamoyl-1,1-dialkyl-methyl)-(S)-prolinamides (94-95%). The enantiomerically pure N-(1-carbamoyl-1,1-dialkyl-methyl)-(S)-prolinamides obtained were tested as organocatalysts for the aldol reaction of cyclohexanone with 4-nitrobenzaldehyde, with yields ranging from 38% to 79% ee. L-proline, organocatalysis;2-aminopropanamides

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