Nucleophilic addition of grignard reagents to 3-acylindoles: stereoselective synthesis of highly substituted indoline scaffolds |
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| Authors: | Lu Wang Yushang Shao Yuanhong Liu |
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| Institution: | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, People's Republic of China, and Department of Chemistry, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, People's Republic of China. |
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| Abstract: | 3-Acylindoles undergo nucleophilic-type reactions with Grignard reagents to efficiently afford either cis- or trans-substituted indolines, depending on the different quenching procedures. The enolate intermediate could be trapped by aryl acyl chlorides to provide indolines bearing a quaternary carbon center with high stereoselectivity. In contrast, the use of benzyl bromide as an electrophile results in the fragmentation of the indole ring. The indoline products could be easily transformed into indoles through oxidation with DDQ in a one-pot manner. |
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