Three-component reactions of isochromenylium tetrafluoroborates via non-classical [4+2]-intermediates: mild one-step metal-free synthesis of functionalized dihydronaphthalenes and tetrahydronaphthalenes |
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Authors: | Hu Zhi-Long Yang Zhen-Yu Wang Shaozhong Yao Zhu-Jun |
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Institution: | State Key Laboratory of Bioorganic and Natural Products Chemistry, EISU Chemical Biology Division, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. |
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Abstract: | Two novel types of elegant three-component reactions of stable isochromenylium tetrafluoroborates (ICTBs) have been developed under mild metal-free conditions in this work. Mechanistically, these reactions are commonly initiated by a 4+2]-cycloaddition between the non-classical isochromenylium diene and the aldehyde-enol, and terminated by the following addition of weak nucleophiles, including nitriles or the second equivalent of aldehydes, in a one-pot fashion. The developed methodologies exhibit excellent chemoselectivity, regioselectivity, and diastereoselectivity, and provide a new convenient access to functionalized dihydronaphthalenes and tetrahydronaphthalenes. |
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Keywords: | aldehydes cascade reactions cycloaddition multicomponent reactions naphthalenes |
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