Stereoselective cycloaddition-lactonization reaction of 2-allyl-4-pentenoic acids with polyfluoroalkyl iodides. An efficient synthesis of polyfluoroalkyl-containing bicyclolactone derivatives |
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| Authors: | Xueyan Yang Wei Pan Wei Cai |
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| Affiliation: | a Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, China
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| Abstract: | Polyfluoroalkyl-containing bicyclolactones were synthesized via the sodium dithionite-initiated cycloaddition-lactonization reaction of 2-allyl-4-pentenoic acids and polyfluoroalkyl iodides. The chemo- and stereo-selectivity of the cycloaddition-lactonization reaction strongly depended on the space hindrance of 2-substituent in 2-allyl-4-pentenoic acids. The reaction was believed to proceed through a tandem free radical addition-lactonization process. |
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| Keywords: | Cycloaddition-lactonization 2-Allyl-4-pentenoic acid Polyfluoroalkyl iodide Bicyclolactone Stereoselectivity |
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