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

Kosuke Nakashima; Yuichi Okuaki; Misaki Deguchi; Yasuyuki Matsushima; Shin-ichi Hirashima; Tsuyoshi Miura

doi:10.1248/cpb.c24-00839

Note

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

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

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Keywords: organocatalyst, asymmetric catalysis, 3,3′-disubstituted oxindole, spirocyclic oxindole

JOURNAL OPEN ACCESS FULL-TEXT HTML

2025 Volume 73 Issue 4 Pages 382-387

DOI https://doi.org/10.1248/cpb.c24-00839

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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.

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