Enantioselective zirconium-catalyzed Friedel-Crafts alkylation of pyrrole with trifluoromethyl ketones.
The first catalytic enantioselective Friedel-Crafts alkylation of pyrrole with 2,2,2-trifluoroacetophenones to give pyrroles with a trifluoromethyl-substituted tertiary alcohol moiety bearing a quaternary stereogenic center is described. The reaction is achieved in the presence of a 3,3'-dibromo-BINOL-Zr(IV) complex to give the expected products with high yields (up to 98%) and good enantioselectivities (up to 93% ee). The absolute stereochemistry of the products has been determined by chemical correlation.
Blay
Gonzalo
G
Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr. Moliner 50, E-46100 Burjassot (Valencia), Spain.
Fernández
Isabel
I
Monleón
Alicia
A
Pedro
José R
JR
Vila
Carlos
C
D000478:Alkylation; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D015040:Zirconium / Q000737:chemistry*
D007659:Ketones; D011758:Pyrroles; D015040:Zirconium