Configuration??Dependent Ring Opening of Silyloxiranes: Synthesis of Functionalized Alkenes or Tetrahydrofurans

J Lange, E Schaumann

文献索引：Lange, Jens; Schaumann, Ernst European Journal of Organic Chemistry, 2009 , # 27 p. 4674 - 4684

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被引用次数: 1

摘要

Abstract cis-and trans-Silyloxiranes with a potential tosylate or bromide leaving group in the β position are available by the diastereospecific reduction of the corresponding alkynes with DIBAL-H and hydrosilylation with silanes, respectively. In the reaction with the anion of a silylthioacetal, the outcome of the reaction is configuration dependent: the cis-oxiranes add nucleophilic methanthiolate and give a cis-vinyl sulfide unit in a Peterson olefination. In ...