Science and Technology Production
Article
Authorship
LAFUENTE, MARÍA LETICIA
;
Maidana, Lautaro
;
Bisceglia, Juan
;
Iribarren, Adolfo
;
Lewkowicz, Elizabeth
Date
2022
Publishing House and Editing Place
GEORG THIEME VERLAG KG
Magazine
SYNTHESIS-STUTTGART
GEORG THIEME VERLAG KG
Summary
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SIGEVA
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 9...
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).
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Key Words
BENZIMIDAZOLEIMIDAZOLIDINONEL-PROLINAMIDEORGANICATALYSISCHIRAL