A Convenient Method for the Synthesis of Alkenes from Vic-diols via Cyclic Sulfates with Magnesium Iodide |
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| Authors: | Doo Ok Jang Yung Hyup Joo |
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| Institution: | 1. Department of Chemistry , Yonsei University , Wonju, 220–710, Korea;2. Pacific Corporation , Pharmaceutical Research Institute , Kyounggi-do, 449–900, Korea |
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| Abstract: | Reaction of cyclic sulfates of vic-diols with magnesium iodide in acetonitrile produced the corresponding olefins in excellent isolated yields at room temperature. Cyclic sulfates of trans-diols gave trans-alkenes exclusively. Cyclic sulfates of cis-diols gave a mixture of cis- and trans- alkenes. However, the cyclic sulfate of cyclic cis-diol afforded the corresponding cis-alkene only. |
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| Keywords: | Wittig reactions Phosphonate carbanions Stereoselective synthesis α β‐Unsaturated esters Carboxylic acids |
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