Enantioselective Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Silyl Ketene Imines with Isatin‐Derived Ketimines |
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| Authors: | Jiannan Zhao Bing Fang Weiwei Luo Xiaoyu Hao Prof?Dr Xiaohua Liu Dr Lili Lin 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 610064 (China);2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China) |
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| Abstract: | A highly enantioselective Mannich reaction of silyl ketene imines with isatin‐derived ketimines has been realized by using a chiral N,N′‐dioxide/ZnII catalyst. A variety of β‐amino nitriles containing congested vicinal tetrasubstituted stereocenters were obtained with excellent outcomes (up to 98 % yield, >19:1 d.r. and 99 % ee). Based on the experimental investigations, a possible transition state has been proposed to explain the origin of the asymmetric induction. |
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| Keywords: | asymmetric synthesis heterocycles homogeneous catalysis synthetic methods zinc |
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