Science and Technology Production
Organocatalytic synthesis of chiral benzimidazole derivatives
Article
Authorship:
LAFUENTE, MARÍA LETICIA ; Maidana, Lautaro ; Bisceglia, Juan ; Iribarren, Adolfo ; Lewkowicz, ElizabethDate:
2022Publishing House and Editing Place:
GEORG THIEME VERLAG KGMagazine:
SYNTHESIS-STUTTGART GEORG THIEME VERLAG KGSummary *
A synthetic route for the production of chiral derivatives of benzimidazole is presented. Different commercially available amines were evaluated as organocatalysts for the stereoselective aldol addition of N-1 benzimidazolyl acetaldehyde, previously prepared by N-alkylation of benzimidazole, with cyclic ketones. When cyclohexanone was used, L-prolinamide proved to be the most efficient catalyst, giving (S)-2-((R)-2-(1H-benzo[d]imidazol-1-yl)-1-hydroxyethyl) cyclohexanone 92% yield, 90% ee and 92:8 dr (anti:syn). Information provided by the agent in SIGEVAKey Words
BENZIMIDAZOLEIMIDAZOLIDINONEL-PROLINAMIDEORGANICATALYSISCHIRAL