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

doi:10.6023/cjoc201903061

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2218-2225.DOI: 10.6023/cjoc201903061 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年；元素有机化学合辑2018-2019

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膦催化α'-亚甲基环戊烯酮的形式[6+2]环加成反应

石崇慧, 肖本现, 杜玮, 陈应春

四川大学华西药学院成都 610041

收稿日期:2019-03-27 修回日期:2019-04-29 发布日期:2019-05-21
通讯作者: 陈应春 E-mail:ycchen@scu.edu.cn
基金资助:
国家自然科学基金（No.21572135）资助项目.

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

Shi Chonghui, Xiao Benxian, Du Wei, Chen Yingchun

West China School of Pharmacy, Sichuan University, Chengdu 610041

Received:2019-03-27 Revised:2019-04-29 Published:2019-05-21
Contact: 10.6023/cjoc201903061 E-mail:ycchen@scu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572135).

1. Phosphine-Catalyzed Formal[6+2] Cycloadditions of α'-Methylene 2-Cyclopentenones.PDF(2459KB)

Abstract

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.

Key words: phosphine catalysis, α'-methylene-2-cyclopentenone, Rauhut-Currier reaction, [6+2]cycloaddition

Cite this article

Shi Chonghui, Xiao Benxian, Du Wei, Chen Yingchun. Phosphine-Catalyzed Formal[6+2] Cycloadditions of α'-Methylene 2-Cyclopentenones[J]. Chin. J. Org. Chem., 2019, 39(8): 2218-2225.

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膦催化α'-亚甲基环戊烯酮的形式[6+2]环加成反应

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

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