Abstract
A chiral phosphoric acid catalyzed highly regio- and enantioselective Friedel-Crafts alkylation at the indole C7-position was developed via the introduction of an alkylamine moiety at the C4-position of the indole ring. The methodology is applicable to a wide range of 4-aminoindoles and β,γ-unsaturated α-ketimino esters to furnish the corresponding C7-position functionalized chiral indole derivatives in high yields with moderate to excellent enantioselectivities. Furthermore, the α-ketimino ester moiety in the products is a versatile building block and enables many further transformations.
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