Stereoselective synthesis of (Z)-fluoroalkenes directed to peptide isosteres: copper mediated reaction of trialkylaluminum with 4,4-difluoro-5-hydroxyallylic alcohol derivatives |
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| Authors: | Yuko Nakamura Azusa Sato Minoru Koura Takeo Taguchi |
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| Institution: | a Tokyo Women's Medical University, 8-1 Kawada-cho, Shinjuku-ku, Tokyo 162-8666, Japan
b Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan |
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| Abstract: | Copper mediated alkyl-transfer reaction of trialkylaluminum (R3Al) with (E)-4,4-difluoro-5-hydroxyallylic alcohol derivative smoothly proceeded to give the corresponding 2-alkylated 4-fluoro-5-hydroxyhomoallylic alcohol derivative with completely Z and 2,5-syn selective manner. Regio- and stereoselective conversion of the C5-hydroxyl group of the fluoroolefin thus obtained to amino group could be achieved through one-pot mesylation and azidation reaction. |
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| Keywords: | Fluoroalkene Difluoroallylic alcohol Trialkylaluminum Cuprous iodide Peptide isosteres |
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