Highly stereoselective synthesis of 6-perfluoroalkyl-6-fluoroalka-2,3,5-(Z)-trienols through carbometallation-elimination of 5-perfluoroalkyl-substituted 4(E)-alken-2-ynols with Grignard reagents |
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| Authors: | Zhichao Ma Yihua Yu |
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| Institution: | a Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People’s Republic of China
b Shanghai Key Laboratory of Functional Magnetic Resonance Imaging, Department of Physics, East China Normal University, Shanghai 200062, People’s Republic of China |
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| Abstract: | A highly regio- and stereoselective sequential carbometallation and Z-selective β-elimination reaction of 5-perfluoroalkyl-4(E)-en-2-ynols with Grignard reagents in Et2O has been developed to afford various 6-perfluoroalkyl-6-fluoroalka-2,3,5(Z)-trienols in good to excellent yields. Primary or secondary alkyl or aryl Grignard reagents may be used to introduce the R2 group to the 2-position of the starting materials referring to the hydroxyl group. A mechanism for this transformation has been proposed. |
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