N-Heterocyclic Carbene-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole-Fused Cyclopentanes

doi:10.6023/cjoc202507009

Chinese Journal of Organic Chemistry

ARTICLE

NHC催化[3+2]环加成反应高非对映选择性地构建环戊酮-螺环氧化吲哚化合物

高源, 刘岩, 李师伍, 唐天胜, 孟钰坤, 赵志飞^*

石河子大学化学化工学院/化工绿色过程省部共建国家重点实验室培育基地新疆石河子 832000

收稿日期:2025-07-08 修回日期:2025-10-09
基金资助:
新疆维吾尔自治区“天池英才”青年博士项目 (No. CZ002737) 和石河子大学 (No. 2022ZK003) 资助项目.

N-Heterocyclic Carbene-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole-Fused Cyclopentanes

Gao Yuan, Liu Yan, Li Shiwu, Tang Tiansheng, Meng Yukun, Zhao Zhifei^*

School School of Chemistry and Chemical Engineering, Shihezi University/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering Shihezi, Xinjiang 832000

Received:2025-07-08 Revised:2025-10-09
Contact: *E-mail: zhaozf@shzu.edu.cn
Supported by:
Tianchi Talent Project of Xinjiang Uygur Autonomous Region (No. CZ002737) and Shihezi University (No. 2022ZK003)

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Abstract

Under N-heterocyclic carbene (NHC) catalysis, a [3+2] cycloaddition reaction between α,β-unsaturated aldehydes and 3-alkenyl oxindoles efficiently constructs spirooxindole-fused cyclopentanes derivatives with three contiguous stereocenters including one spirocarbon center. This transformation demonstrates broad substrate scope, delivering products with moderate to good yields (43%-78%) and excellent diastereoselectivity (>20:1 dr). The protocol features mild reaction conditions, operational simplicity, and scalability to gram-level synthesis. This study establishes a novel synthetic methodology for the efficient construction of functionalized spirooxindole-fused cyclopentanes.

Key words: N-heterocyclic carbene, cycloaddition, 3-alkenyl oxindole, spirooxindole-fused cyclopentanes

Cite this article

Gao Yuan, Liu Yan, Li Shiwu, Tang Tiansheng, Meng Yukun, Zhao Zhifei. N-Heterocyclic Carbene-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole-Fused Cyclopentanes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202507009.

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NHC催化[3+2]环加成反应高非对映选择性地构建环戊酮-螺环氧化吲哚化合物

N-Heterocyclic Carbene-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole-Fused Cyclopentanes

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