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1,4-Hydroiodination of Dienyl Alcohols with TMSI To Form Homoallylic Alcohols Containing a Multisubstituted Z‑Alkene and Application to Prins Cyclization

Yongjin Xu,Zhiping Yin,Xinglong Lin,Zubao Gan,Yanyang He,Lu Gao,Zhenlei Song

Organic Letters（2015）

Cited 15|Views4
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Abstract
A regioselective 1,4-hydroiodination of dienyl alcohols has been developed using trimethylsilyl iodide as Lewis acid and iodide source. A range of homoallylic alcohols containing a multisubstituted Z-alkene was synthesized with good to excellent configurational control. The approach was applied in sequential hydroiodination/Prins cyclization to afford multisubstituted tetrahydropyrans diastereoselectively.
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halogenation
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