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Synthesis and characterization of optically active camphor-anelated imidazolines.

Authors: Tydlitát Jiří | Bureš Filip | Kulhánek Jiří

Year: 2012

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Synthesis and characterization of optically active camphor-anelated imidazolines.	Optically active imidazolines constitute attractive five-membered heterocycles. Due to the presence of two nitrogens, they are able to coordinate various transition metals and such complexes found wide application in asymmetric reactions. The main aim of the presented work is to synthesize and fully characterize camphor anelated imidazoline ligands with various pendants at C2 of the imidazoline. The synthesis starts with either base or acid catalyzed conversion of (hetero)aromatic nitriles to the corresponding imidates. The imidates were treated with (1R,2R)-camphordiamine dihydrochloride to yield NH-imidazolines. The generated NH-imidazolines were further N modified by benzoylation. This reaction step involves deprotonation using LHMDS and subsequent quench of the lithiated species with 4 methoxybenzoylchloride to afford the desired N-substituted imidazolines as a pair of two separable regioisomers. Following the afore-mentioned synthetic pathway, we have prepared seven chiral camphor-anelated imidazolines with various coordinating auxiliaries R such as pyrimidine 2 yl, pyrazine 2 yl, isochinoline 1 yl, 1H pyrrole 2 yl, thiophene 2 yl, pyridine 2,6 diyl and phenyl. From those camphor-anelated imidazolines we have prepared and separated eight regioisomers, all of them we have applied in copper catalyzed Henry reaction.	imidazolin; terpen; syntéza; asymmetrická katalýza