Asymmetric Ring‐Opening of Cyclopropyl Ketones with Thiol,Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral N,N′‐Dioxide–Scandium(III) Complex |
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| Authors: | Yong Xia Dr Lili Lin Fenzhen Chang Xuan Fu Prof Dr Xiaohua Liu 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);3. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China) |
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| Abstract: | A highly efficient asymmetric ring‐opening reaction of cyclopropyl ketones with a broad range of thiols, alcohols and carboxylic acids has been first realized by using a chiral N,N′‐dioxide–scandium(III) complex as catalyst. The corresponding sulfides, ethers, and esters were obtained in up to 99 % yield and 95 % ee. This is also the first example of one catalytic system working for the ring‐opening reaction of donor–acceptor cyclopropanes with three different nucleophiles, let alone in an asymmetric version. |
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| Keywords: | asymmetric catalysis cyclopropyl ketones nucleophiles ring opening scandium catalysts |
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