Naslov
Aldol reaction of 1, 4-benzodiazepin-2-one with the derivatives of 2-methyl-cinnamaldehydes and stereoselective hydrogenation of double bond in syn/anti aldol reaction

Autori
Gašo-Sokač, Dajana ; Kovač, Spomenka ; Šunjić, Vitomir ; Hameršak, Zdenko

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
XVIII. hrvatski skup kemičara i kemijskih inženjera : Sažeci = Abstracts / Zrnčević, Stanka - Zagreb : Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI) ; Hrvatsko kemijsko drustvo ; Hinus, 2003, 100-100

ISBN
953-6894-08-4

Skup
Hrvatski skup kemičara i kemijskih inženjera (18 ; 2003)

Mjesto i datum
Zagreb, Hrvatska, 16.02.2003. - 19.02.2003

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
aldol reaction ; 1 ; 4-benzodiazepin-2-one

Sažetak
Diastereomeric mixtures of 3-substituted 7- chloro-2, 3-dihidro-1-methyl-5-phenyl-1H-1, 4- benzodiazepin-2-ones (1-8) have been prepared by aldol reaction of C(3) carbanion of benzodiazepin-2-one with para-substituted 2- methyl-cinnamaldehydes. Syn and anti diastereomeres have been separated by column chromatography and the relative configuration has been determined by 1H NMR spectroscopy. Diastereoselectivity of hydrogenation of double bond in diastereomeric racemates 3-8 was studied. Rh complexes with achiral (DIPHOS-4) and chiral ligand (CHIRAPHOS) found to be effective catalysts, and diastereomers 9-17 have been prepared. Hydrolysis of racemate 14 afforded 2-benzyloxycarbonylamino-5-(4-chloro- phenyl)-3-hydroxy-4-methyl-pentanoic acid, a first representative of this class of non- natural  ; -amino- ; -hydroxy- ; -methyl carboxylic acid

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biotehnologija

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