1,4-Hydroiodination of dienyl alcohols with TMSI to form homoallylic alcohols containing a multisubstituted Z-alkene and application to Prins cyclization.

Authors :: Xu Y
Yin Z
Lin X
Gan Z
He Y
Gao L
Song Z
Source :: Organic letters [Org Lett] 2015 Apr 17; Vol. 17 (8), pp. 1846-9. Date of Electronic Publication: 2015 Mar 31.
Publication Year :: 2015
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.

Subjects :: Cyclization
Molecular Structure
Pyrans chemistry
Alcohols chemical synthesis
Alcohols chemistry
Alkenes chemistry
Pyrans chemical synthesis
Trimethylsilyl Compounds chemistry

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