title: Enantioselective indole Friedel--Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes.
abstract: 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.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
authors.forename: David A
authors.initials: DA
authors.lastname: Evans
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
authors.forename: Keith R
authors.initials: KR
authors.lastname: Fandrick
authors.forename: Hon Wai
authors.initials: HW
authors.lastname: Lam
authors.forename: Jimmy
authors.initials: J
authors.lastname: Wu
mesh_terms: 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
chemical_list: D007211:Indoles; D008698:Mesylates; D063065:Organophosphonates; D010080:Oxazoles; D011725:Pyridines; C436603:scandium triflate; C064210:oxazolidine; D012538:Scandium