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Enantioselective Indole Friedel−Crafts Alkylations Catalyzed by Bis(oxazolinyl)pyridine−Scandium(III) Triflate Complexes

Journal of the American Chemical SocietyPublished 13 August 2003
David A. Evans, Karl A. Scheidt, Keith R. Fandrick, Hon Wai Lam, Jimmy Wu
Citations219
SJR quartileQ1
SJR score5.55
SNIP2.61

TL;DR

A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished.

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.

Keywords

ChemistryBiochemistry, Genetics and Molecular Biology