Enantioselective Conjugate Addition of Alkenyl Trifluoroborates to Alkenyl-Substituted Benzimidazoles Catalyzed by Chiral Binaphthols.

ABSTRACT

The enantioselective organocatalytic conjugate alkenylation of ß-substituted alkenyl benzimidazoles afforded ß-stereogenic 2-alkyl benzimidazole derivatives in excellent enantioselectivities. Chiral binaphthols were effective catalysts for promoting the nucleophilic addition of bench-stable alkenyl trifluoroborate salts under mild conditions, expanding their applications by utilizing C=N-containing azaarenes as activating groups. The synthetic utility of this strategy is demonstrated by conversions into several useful enantiomerically enriched benzimidazole building blocks.