Asymmetric Synthesis of 2,3‐Dihydropyrroles by Ring‐Opening/Cyclization of Cyclopropyl Ketones Using Primary Amines |
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| Authors: | Yong Xia Prof?Dr Xiaohua Liu Haifeng Zheng Dr Lili Lin Prof?Dr Xiaoming Feng |
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| Affiliation: | 1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China);2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China) |
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| Abstract: | The asymmetric ring‐opening/cyclization of cyclopropyl ketones with primary amine nucleophiles was catalyzed by a chiral N,N′‐dioxide/scandium(III) complex through a kinetic resolution process. A broad range of cyclopropyl ketones and primary amines are suitable substrates of this reaction. The corresponding products were afforded in excellent enantioselectivities and yields (up to 97 % ee and 98 % yield) under mild reaction conditions. This method provides a promising access to chiral 2,3‐dihydropyrroles as well as an effective procedure for the kinetic resolution of 2‐substituted cyclopropyl ketones. |
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| Keywords: | cyclization kinetic resolution N N′ ‐dioxides ring opening scandium |
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