Publication detail

Design and Efficient Synthesis of Amino Acid Derived 2-Substituted Imidazoles by Palladium-Catalyzed Cross-Coupling Reactions

Authors: Marek Aleš | Kulhánek Jiří | Bureš Filip

Year: 2009

Type of publication: článek v odborném periodiku

Name of source: Synthesis

Publisher name: Georg Thieme Verlag KG

Place: Stuttgart

Page from-to: 325-332

Titles:

Language	Name	Abstract	Keywords
cze	Design a syntéza 2-substituovaných derivátů imidazolu a amino kyselin paladiem katalyzovanými cross-coupling reakcemi	Opticky aktivní deriváty imidazolu s motivem amino kyselin a substituovanými v poloze 2 lze připravovat pomocí Negishi nebo Suzuki-Miyaura cross-coupling reakcemi. Reakční sekvence zahrnuje N-protekci (ethoxymethylaci), kdy vzniklé regioisomery lze dělit pomocí sloupcové chromatografie, selektivní lithiaci v poloze 2 následovanou transmetalací na zinek nebo reakcí s jodem a Negishi nebo Suzuki-Miyaura reakci s (hetero)aromáty.	imidazol; cross-coupling; amino kyselina
eng	Design and Efficient Synthesis of Amino Acid Derived 2-Substituted Imidazoles by Palladium-Catalyzed Cross-Coupling Reactions	Optically active imidazole derivatives featuring an aamino acid motive substituted at the 2-position can be prepared in moderate to good yields by Negishi as well as Suzuki?Miyaura cross-couplings as the key synthetic steps. The reaction sequence involves N-protection (ethoxymethylation), whereby both generated regioisomers could be separated by column chromatography, and selective 2-lithiation. Subsequent transmetalation to zinc or an iodine quench affords reactants suitable for Pd-catalyzed Negishi and Suzuki?Miyaura reactions with (hetero)aromatics.	imidazole; cross-coupling; amino acid

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