Citation: Min Liu, Di Wang, Zenghui Ye, Donghao Jiang, Bencan Tang, Yanqi Wu, Fengzhi Zhang. Highly stereo- and enantio-selective synthesis of spiro cyclopropyl oxindoles via organic catalyst-mediated cyclopropanation[J]. Chinese Chemical Letters, ;2025, 36(10): 110923. doi: 10.1016/j.cclet.2025.110923 shu

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

Min Liu ^{a, b, 1} ,
Di Wang ^{c, 1} ,
Zenghui Ye ^{d, 1} ,
Donghao Jiang ^b ,
Bencan Tang ^{c, *,} ,
Yanqi Wu ^{d, *,} ,
Fengzhi Zhang ^{d, *,}

a.
School of Life Science, Huzhou University, Huzhou 313000, China
b.
School of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310000, China
c.
Department of Chemical and Environment Engineering, The University of Nottingham Ningbo China, Ningbo 315100, China
d.
School of Pharmacy, Hangzhou Medical College, Hangzhou 311399, China

bencan.tang@nottingham.edu.cn

wuyanqi@hmc.edu.cn

fengzhi_zhang@hotmail.com

Received Date: 20 July 2024
Revised Date: 13 January 2025
Accepted Date: 5 February 2025
Available Online: 6 February 2025

Figures(6)

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.
- Spiro-cyclopropyl oxindoles,
- Asymmetric synthesis,
- Tandem reaction,
- Ammonium ylides,
- Michael addition
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