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

doi:10.6023/cjoc202507009

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (3): 1008-1016.DOI: 10.6023/cjoc202507009 Previous Articles Next Articles

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氮杂环卡宾(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 发布日期:2025-11-27
通讯作者: 赵志飞
基金资助:
新疆维吾尔自治区“天池英才”青年博士项目和石河子大学(2022ZK003)

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

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

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

Received:2025-07-08 Revised:2025-10-09 Published:2025-11-27
Contact: Zhifei Zhao
Supported by:
Tianchi Talent Project of Xinjiang Uygur Autonomous Region and Shihezi University(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 constructed spirooxindole-fused cyclopentane 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 cyclopentane

Cite this article

Yuan Gao, Yan Liu, Shiwu Li, Tiansheng Tang, Yukun Meng, Zhifei Zhao. N-Heterocyclic Carbene (NHC)-Catalyzed [3＋2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole-Fused Cyclopentanes[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 1008-1016.

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Fig. & Tab. 6

References 9

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Entry	Catalyst	Base	Solvent	T/℃	Yield^b/%	dr^c
1	A	K₂CO₃	THF	25	Trace	—
2	B	K₂CO₃	THF	25	58	20∶1
3	C	K₂CO₃	THF	25	Trace	—
4	D	K₂CO₃	THF	25	Trace	—
5	E	K₂CO₃	THF	25	Trace	—
6	B	Na₂CO₃	THF	25	78	20∶1
7	B	Cs₂CO₃	THF	25	62	20∶1
8	B	NaOH	THF	25	60	20∶1
9	B	t-BuOK	THF	25	40	20∶1
10	B	K₃PO₄	THF	25	71	20∶1
11	B	Et₃N	THF	25	Trace	—
12	B	Na₂CO₃	Toluene	25	Trace	—
13	B	Na₂CO₃	CH₃CN	25	Trace	—
14	B	Na₂CO₃	DCM	25	Trace	—
15	B	Na₂CO₃	THF	0	0	Trace
16	B	Na₂CO₃	THF	40	61	20∶1

Entry	Catalyst	Base	Solvent	T/℃	Yield^b/%	dr^c
1	A	K₂CO₃	THF	25	Trace	—
2	B	K₂CO₃	THF	25	58	20∶1
3	C	K₂CO₃	THF	25	Trace	—
4	D	K₂CO₃	THF	25	Trace	—
5	E	K₂CO₃	THF	25	Trace	—
6	B	Na₂CO₃	THF	25	78	20∶1
7	B	Cs₂CO₃	THF	25	62	20∶1
8	B	NaOH	THF	25	60	20∶1
9	B	t-BuOK	THF	25	40	20∶1
10	B	K₃PO₄	THF	25	71	20∶1
11	B	Et₃N	THF	25	Trace	—
12	B	Na₂CO₃	Toluene	25	Trace	—
13	B	Na₂CO₃	CH₃CN	25	Trace	—
14	B	Na₂CO₃	DCM	25	Trace	—
15	B	Na₂CO₃	THF	0	0	Trace
16	B	Na₂CO₃	THF	40	61	20∶1

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氮杂环卡宾(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 (NHC)-Catalyzed [3＋2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole-Fused Cyclopentanes

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