Stereoselective double Friedel-Crafts alkylation of indoles with divinyl ketones.
A tandem double Friedel-Crafts reaction of indoles and nonsymmetrical divinyl ketones has been achieved. The tandem reaction forms complex [6-5-7]-tricyclic indoles in excellent yields. The reaction is completely regioselective and offers high levels of syn diastereoselectivity. The reaction is also seen to be sensitive to substrate structure and catalyst.
Silvanus
Andrew C
AC
Department of Chemistry, University of Bath, Bath BA2 7AY, UK.
Heffernan
Stephen J
SJ
Liptrot
David J
DJ
Kociok-Köhn
Gabriele
G
Andrews
Benjamin I
BI
Carbery
David R
DR
D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D007211:Indoles; D007659:Ketones