Work

Rapid Access to an Enantioenriched Spiro Bisindole Directly from Indole and Acetone

Year: 2025

Type: article

Abstract: Disclosed here is a “one‐pot self‐assembly” strategy for the enantioselective synthesis of a spiro bisindole molecule directly from indole and acetone. This convenient synthesis contrasts drastically to the typical long sequence required for other privileged C 2 ‐symmetric spirocycles. The use of an alcohol additive in cooperation with chiral phosphoric acid (CPA) catalysis proved crucial to the good efficiency and enantioselectivity. The favorable interaction between the additive and CPA was confirmed by nuclear magnetic resonance (NMR) and density functional theory (DFT) studies. The obtained enantiopure C 2 ‐symmetric bisindole was demonstrated as a useful backbone of chiral catalysts/ligands.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202507798

Authors: Jing‐Yi Wang, Jie Lin, Chaoshen Zhang, Jianwei Sun

Institution: Hong Kong University of Science and Technology

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: National Natural Science Foundation of China, Innovation and Technology Commission