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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

Author:
Xu, Yongjin, Yin, Zhiping, Lin, Xinglong, Gan, Zubao, He, Yanyang, Gao, Lu, Song, Zhenlei
Source:
Organic letters 2015 v.17 no.8 pp. 1846-1849
ISSN:
1523-7052
Subject:
Lewis acids, alcohols, chemical reactions, chemical structure, diastereoselectivity, iodides, organoiodine compounds, regioselectivity
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.
Agid:
5790453