Asymmetric Ring Opening/Cyclization/Retro‐Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2‐Diamines for the Synthesis of Benzimidazole Derivatives |
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| Authors: | Yong Xia Dr Lili Lin Fenzhen Chang Yuting Liao Prof Dr Xiaohua Liu Prof Dr Xiaoming Feng |
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| Institution: | 1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China;2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China |
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| Abstract: | A highly efficient asymmetric ring‐opening/cyclization/retro‐Mannich reaction of cyclopropyl ketones with aryl 1,2‐diamines has been realized using a chiral N,N′‐dioxide/ScIII catalyst. Benzimidazoles containing chiral side chains were generated under mild reaction conditions in excellent outcomes (up to 99 % yield and 97 % ee). This method also provides efficient access to chiral benzimidazole‐substituted amide and cycloheptene derivatives. |
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| Keywords: | asymmetric catalysis enantioselectivity heterocycles scandium small ring systems |
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