Synthesis of chiral N-alkylated indoles through replacement of aniline nitrogen by natural amino acids

Abstract

Chiral N-alkylated indoles are privileged structural motifs found in many natural products and pharmaceuticals and a search for effective methods with which to prepare chiral N-alkylated indoles is ongoing. Efficient syntheses of enantioenriched N-alkylated indoles has been developed but not with standing these advances, the development of a facile method to prepare chiral N-alkylated indoles from simple and available starting materials under mild conditions is still needed. In this paper, we report a nitrogen replacement process driven by dearomatization that directly incorporates natural α-amino acids into 2-alkynylanilines leading to the formation of a variety of multi-functional chiral N-alkylated indoles.