Chiral Brønsted acid catalyzed asymmetric Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated ketones: short access to optically active 2- and 3-substituted indole derivatives.
The asymmetric Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated ketones catalyzed by chiral phosphoric acid is reported. A wide range of indoles and 4,7-dihydroindoles were allowed to react with α,β-unsaturated ketones to give the corresponding 1,4-adducts in good to high chemical yields and with excellent enantioselectivities.
Sakamoto
Tsubasa
T
Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
Itoh
Junji
J
Mori
Keiji
K
Akiyama
Takahiko
T
D000143:Acids / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000143:Acids; D007211:Indoles; D007659:Ketones