Citation: Shi Chonghui, Xiao Benxian, Du Wei, Chen Yingchun. Phosphine-Catalyzed Formal[6+2] Cycloadditions of α'-Methylene 2-Cyclopentenones[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2218-2225. doi: 10.6023/cjoc201903061 shu

Phosphine-Catalyzed Formal[6+2] Cycloadditions of α'-Methylene 2-Cyclopentenones

West China School of Pharmacy, Sichuan University, Chengdu 610041

Corresponding author: Chen Yingchun, ycchen@scu.edu.cn
Received Date: 27 March 2019
Revised Date: 29 April 2019
Available Online: 21 August 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21572135)the National Natural Science Foundation of China 21572135

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The formal[6+2] cycloaddition reaction of α'-methylene-2-cyclopentenones and 2-alkylidene-1, 3-indanediones was developed under the catalysis of tricyclohexyl phosphine, proceeding in a remote γ-regioselective Rauhut-Currier-type reaction followed by a β'-regioselective intramolecular Michael addition process. An array of fused bicyclic frameworks incorperating a spiro-1, 3-indanedione motif were produced in fair to good yields of 48%~76% with excellent diastereoseletivity (generally>19:1 dr). This protocol expands the reaction mode of traditional Rauhut-Currier reaction, which might find further application in organic synthesis.
- phosphine catalysis,
- α'-methylene-2-cyclopentenone,
- Rauhut-Currier reaction,
- [6+2]cycloaddition
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