Enantioselective indole Friedel--Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.
A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished. The reaction involves alpha,beta-unsaturated acyl phosphonates as electrophiles and primarily substituted indoles as nucleophiles. The reactive acyl phosphonate product is converted to the corresponding ester or amide in good overall yield by adding an alcohol or amine directly to the reaction mixture.
Evans
David A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Scheidt
Karl A
KA
Fandrick
Keith R
KR
Lam
Hon Wai
HW
Wu
Jimmy
J
D000478:Alkylation; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis*; D008698:Mesylates / Q000737:chemistry*; D008958:Models, Molecular; D063065:Organophosphonates / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
D007211:Indoles; D008698:Mesylates; D063065:Organophosphonates; D010080:Oxazoles; D011725:Pyridines; C436603:scandium triflate; C064210:oxazolidine; D012538:Scandium