Work

Highly stereo- and enantio‑selective synthesis of spiro cyclopropyl oxindoles via organic catalyst-mediated cyclopropanation

Year: 2025

Type: article

Abstract: Spiro-cyclopropyl oxindoles are widely found in natural products and medicinal molecules. Herein, we report a highly stereo- and enantio‑selective procedure for accessing this class of compounds via tertiary amine mediated cyclopropanation of ammonium ylides with the in-situ Heck reaction-generated 3-alkenyl indolones as the Michael receptors. This reaction features mild conditions, excellent enantioselectivity (up to 98%) and diastereoselectivity (up to 99:1), high atom- and step-economy, broad substrate scopes, and good functional group tolerance. Additionally, this scalable synthetic process could offer a novel strategy for the efficient synthesis of enantiopure spirocyclopropyl oxindoles.

Source: Chinese Chemical Letters

DOI: 10.1016/j.cclet.2025.110923

Authors: Min Liu, Di Wang, Zenghui Ye, Donghao Jiang, Bencan Tang, Yanqi Wu, Fengzhi Zhang

Institutions: Huzhou Normal University, Zhejiang University of Technology, University of Nottingham Ningbo China, Hangzhou Medical College

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

OpenAlex ID: W4407196388

FWCI: 0.894

Cites: 60

Cited by: 3

Related to: 10