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Asymmetric Synthesis of 3-Spiro-Fused 2-Oxindoles via Organocatalyst/N-Iodosuccinimide/Hydrogen Peroxide-Mediated Oxidative Cyclization

Year: 2025

Type: article

Abstract: A squaramide organocatalyst was employed to efficiently promote asymmetric oxidative lactonization to construct spiro-fused 2-oxindoles in moderate-to-good yield and enantioselectivity (up to 81% enantiomeric excess (ee)). Herein, we report the first study accomplishing stereoselective oxidative cyclization from indole propionic acid using an organocatalyst, N-iodosuccinimide (NIS), and hydrogen peroxide under metal-free and mild reaction conditions.

Source: Chemical and Pharmaceutical Bulletin

DOI: 10.1248/cpb.c24-00839

Authors: Kosuke Nakashima, Yuichi Okuaki, Misaki Deguchi, Yasuyuki Matsushima, Shin-ichi Hirashima, Tsuyoshi Miura

Institution: Tokyo University of Pharmacy and Life Sciences

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

OpenAlex ID: W4409632817

FWCI: 0.298

Cites: 30

Cited by: 1

Related to: 10