Journal
ACS CATALYSIS
Volume 8, Issue 1, Pages 349-353Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03708
Keywords
chiral Bronsted acid; aza-Friedel-Crafts reaction; indole; ketimine; sulfonic acid
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Funding
- JSPS [JPI5H05755, JP17H03054, JP15H05810]
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The enantioselective aza-Friedel Crafts reaction of indoles with low-reactive ketimines has been developed in the presence of a chiral monopotassium binaphthyldisulfonate as a strong Bronsted acid catalyst. A broad substrate scope was achieved, and the corresponding 3-indolylmethanamines with a chiral quaternary carbon center were obtained in high yields with high enantioselectivities. The addition of a catalytic amount of acetic acid considerably promoted the reaction, and a gram-scale reaction could be achieved with reduced catalyst loading.
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