Stereoselective synthesis of (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides by base-promoted ring-opening of iodomethylated epoxides |
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| Authors: | Takahiro Ichige |
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| Institution: | Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan |
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| Abstract: | Both (E)- and (Z)-3-hydroxy-2-methyl-1-alkenyl iodides were stereoselectively synthesized from iodomethylated epoxides by treatment with sodium hexamethyldisilazane in DMF and with LDA in THF (or lithium 2,2,6,6-tetramethylpiperidide in THF), respectively. |
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| Keywords: | Vinyl iodides Epoxides Base-promoted ring-opening Syn elimination Anti elimination |
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