Stereoselective synthesis of (e)-2-alkene-1,4-diols via metallated allylic sulphoxides |
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Affiliation: | 1. State Key Laboratory of Water Resources and Hydropower Engineering Science, Wuhan University, Wuhan, China;2. Department of Civil and Environment Engineering, The Hong Kong University of Science and Technology, Kowloon, Clear Water Bay, Hong Kong;3. China Building Materials Academy, Beijing, China;4. Institute of Construction Sciences Eduardo Torroja, Madrid, Spain |
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Abstract: | Reaction of allyl sulphinyl anion with chiral α-methylaldehydes affords α- or γ-adducts in highly regio-controlled fashion, depending on reaction conditions. From the α-adducts (E)-2-alkene-1,4-diols are obtained as major (d.r. 2:1 ~ 28:1) products by thiophile promoted desulphurization. |
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