Catalytic Asymmetric Friedel-Crafts Alkylation of β,γ-Unsaturated α-Ketoesters: Enantioselective Addition of Aromatic C-H Bonds to Alkenes.

Abstract

Useful catalytic BOXes: Chiral bisoxazoline (BOX)/Lewis acid complexes can catalyze highly enantioselective Friedel–Crafts alkylation reactions. The new reaction (see scheme) is successful with both aromatic and heteroaromatic compounds and with a wide range of β,γ-unsaturated α-ketoesters (R1 = alkyl, aryl, or a protected alcohol). Products are formed with up to >99 % ee.