Copper‐Catalyzed Enantioselective Arylative Desymmetrization of Prochiral Cyclopentenes with Diaryliodonium Salts |
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| Authors: | Dr Hua Wu Dr Qian Wang Prof?Dr Jieping Zhu |
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| Institution: | 1. http://lspn.epfl.ch;2. Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland |
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| Abstract: | A copper‐catalyzed enantioselective arylative desymmetrization of prochiral cyclopentenes with diaryliodonium salts was developed. In the presence of a catalytic amount of a chiral copper–bisoxazoline complex, which was generated in situ, the reaction of 4‐substituted or 4,4‐disubstituted cyclopent‐1‐enes with diaryliodonium hexafluoroarsenates afforded the chiral arylated products in good yields with excellent enantioselectivity. A cyclohexyl‐containing Box ligand was essential for the high enantioselectivity. Transformation of the enantiomerically enriched adducts into other chiral building blocks is also documented. |
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| Keywords: | asymmetric synthesis desymmetrization diaryliodonium salts Heck reaction homogeneous catalysis |
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