Isoprene-Mediated Lithiation of 1-Alkylimidazoles: Chiral Induction of the Alkyl Substituent

Title: Isoprene-Mediated Lithiation of 1-Alkylimidazoles: Chiral Induction of the Alkyl Substituent

Volume: 7 Issue: 5

Author(s): Isidro M. Pastor, Rosario Torregrosa and Miguel Yus

Affiliation:

Keywords: Isoprene-mediated lithiation, imidazole derivatives, nucleophilic addition, lithium

Abstract: The isoprene-mediated lithiation of imidazoles bearing a secondary alkyl substituent at the nitrogen (7, 8 and 13) and the subsequent nucleophilic addition to different electrophiles allows the preparation of the corresponding 2- functionalized imidazoles 10, 11 and 14. The presence of a stereogenic center in the alkyl substituent induces diastereoselection during the nucleophilic addition step with a prochiral electrophile (i.e. pivalaldehyde), producing the expected imidazole derivative with excellent overall yield, but low de (up to 26%).

Cite this article as:

M. Pastor Isidro, Torregrosa Rosario and Yus Miguel, Isoprene-Mediated Lithiation of 1-Alkylimidazoles: Chiral Induction of the Alkyl Substituent, Letters in Organic Chemistry 2010; 7 (5) . https://dx.doi.org/10.2174/157017810791514850