Desilylation‐Activated Propargylic Transformation: Enantioselective Copper‐Catalyzed [3+2] Cycloaddition of Propargylic Esters with β‐Naphthol or Phenol Derivatives |
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| Authors: | Long Shao Ya‐Hui Wang De‐Yang Zhang Prof Dr Jie Xu Prof Dr Xiang‐Ping Hu |
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| Institution: | 1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China;2. University of Chinese Academy of Sciences, Beijing, China |
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| Abstract: | A copper‐catalyzed asymmetric 3+2] cycloaddition of 3‐trimethylsilylpropargylic esters with either β‐naphthols or electron‐rich phenols has been realized and proceeds by a desilylation‐activated process. Under the catalysis of Cu(OAc)2?H2O in combination with a structurally optimized ketimine P,N,N‐ligand, a wide range of optically active 1,2‐dihydronaphtho2,1‐b]furans or 2,3‐dihydrobenzofurans were obtained in good yields and with high enantioselectivities (up to 96 % ee). This represents the first desilylation‐activated catalytic asymmetric propargylic transformation. |
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| Keywords: | asymmetric catalysis cycloaddition copper heterocycles reaction mechanisms |
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