Convenient stereoselective synthesis of 3-hydroxy-2-iodo-2(E)-alkenyl sulfides via iodohydroxylation of 1,2-allenyl sulfoxides in the presence of BnSH |
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| Authors: | Chunling Fu Shengming Ma |
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| Institution: | a Laboratory of Molecular Synthesis and Recognition, Department of Chemistry, Zhejiang University, 310027 Hangzhou, Zhejiang, PR China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China |
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| Abstract: | The iodohydroxylation of 1,2-allenyl sulfoxides with I2 in the presence of BnSH affords 3-hydroxy-2-iodo-2(E)-alkenyl sulfides in good yields and selectivities. The stereochemistry for the products of this transformation is opposite to what was obtained from the iodohydroxylation of 1,2-allenyl sulfides. Based on the results of some control experiment, a mechanism was proposed. |
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| Keywords: | Allenes Sulfoxides Iodohydroxylation |
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