Bimetallic Gold(I)/Chiral N,N′‐Dioxide Nickel(II) Asymmetric Relay Catalysis: Chemo‐ and Enantioselective Synthesis of Spiroketals and Spiroaminals |
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| Authors: | Jun Li Dr Lili Lin Bowen Hu Xiangjin Lian Gang Wang Prof?Dr Xiaohua Liu Prof?Dr Xiaoming Feng |
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| Institution: | 1. Key Laboratory of Green Chemistry and 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 cascade reaction between keto esters and alkynyl alcohols and amides is reported. The success of the reaction was attributed to the combination of chiral Lewis acid N,N′‐dioxide nickel(II) catalysis with achiral π‐acid gold(I) catalysis working as an asymmetric relay catalytic system. The corresponding spiroketals and spiroaminals were synthesized in up to 99 % yield, 19:1 d.r., and more than 99 % ee under mild reaction conditions. Control experiments suggest that the N,N′‐dioxide ligand was essential for the formation of the spiro products. |
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| Keywords: | asymmetric catalysis cascade reactions gold nickel relay catalysis |
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