Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple alpha,beta-unsaturated ketones.
[structure: see text]. The first general and highly enantioselective organocatalytic Friedel-Crafts alkylation of indoles with simple alpha,beta-unsaturated ketones has been accomplished. Central to these studies has been the identification of a new catalyst amine salt, in which both the cation and the anion are chiral, that exhibits high reactivity and selectivity for iminium ion catalysis.
Bartoli
Giuseppe
G
Dipartimento di Chimica Organica A Mangini, Alma Mater Studiorum, Università di Bologna, Viale Risorgimento 4, 40136 Bologna, Italy.
Bosco
Marcella
M
Carlone
Armando
A
Pesciaioli
Fabio
F
Sambri
Letizia
L
Melchiorre
Paolo
P
D000478:Alkylation; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D007097:Imines; D007211:Indoles; D007659:Ketones