Univerzita PardubiceFakulta chemicko- technologická

Univerzita Pardubice

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Publikace detail

CBZ-PROTECTED α-AMINO ACID-DERIVED IMIDAZOLES AND BENZIMIDAZOLES

Autoři: Podlesný Jan | Bureš Filip

Rok: 2012

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

Tituly:

Jazyk	Název	Abstrakt	Klíčová slova
eng	CBZ-PROTECTED α-AMINO ACID-DERIVED IMIDAZOLES AND BENZIMIDAZOLES	Nowadays, α-amino acid-derived heterocyclic derivatives constitute a very important class of organic compounds due to their promising application as ligands in variety of asymmetric reactions, starting material for construction of larger systems, and in medicinal chemistry. We have recently synthesized chiral 2-phenylimidazoles 1 and benzo[d]imidazole derivatives 2 containing α-amino acid residue appended either at the positions C4(C5) or C2. Straightforward synthesis of 1-2 starts from Cbz protected α-amino acids, their activation via mixed anhydride, and subsequent reaction with benzamidine or benzene 1,2-diamine. These reaction afforded 2-phenylimidazoles 1 and amides that were further condensed to benzo[d]imidazoles 2. Further elaboration on 2 by N-methylation yielded new (poly)alkylated products that will be discussed in details. Preliminary application of 1-2 as nitrogen ligands in the Cu(II)-catalyzed asymmetric version of Henry reaction will be also presented.	imidazole; α-amino acid; ligand