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Updated: Oct 25, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Organocatalytic Asymmetric Friedel-Crafts Reaction-Cyclization-Elimination Cascade for Atroposelective Construction
Ramji Meher1, Dipali Digangana Sahoo1, Poulome Maji1
1Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati, Assam781039, India.
Abstract:
Atroposelective indole formation is an efficient method for the preparation of indole-based biaryls. Herein, a protocol for a convenient organocatalytic asymmetric synthesis of 3,3'-biindole derivatives has been developed via an asymmetric Friedel-Crafts reaction-cyclization-elimination cascade employing indole based α-hydroxyl ketone and N-phenyl-2-naphthylamine. This method constitutes a rare central-to-axial chirality conversion (CACC) technique without the requirement of additional reagent. The reaction was catalyzed by chiral phosphoric acid and 3,3'-biindole compounds were effectively produced with high yields and enantioselectivities (up to 93% yield, 97:3 er). With water as the only byproduct, this method offers a convergent synthetic strategy for the enantioselective synthesis of axially chiral 3,3'-biiindole frameworks.
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