title: 1,4-Hydroiodination of dienyl alcohols with TMSI to form homoallylic alcohols containing a multisubstituted Z-alkene and application to Prins cyclization.
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.
authors.affiliation: † Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡ State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. China.
authors.forename: Yongjin
authors.initials: Y
authors.lastname: Xu
authors.affiliation: † Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡ State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. China.
authors.forename: Zhiping
authors.initials: Z
authors.lastname: Yin
authors.affiliation: † Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡ State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. China.
authors.forename: Xinglong
authors.initials: X
authors.lastname: Lin
authors.affiliation: † Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡ State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. China.
authors.forename: Zubao
authors.initials: Z
authors.lastname: Gan
authors.affiliation: † Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡ State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. China.
authors.forename: Yanyang
authors.initials: Y
authors.lastname: He
authors.affiliation: † Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡ State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. China.
authors.forename: Lu
authors.initials: L
authors.lastname: Gao
authors.affiliation: † Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, and ‡ State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. China.
authors.forename: Zhenlei
authors.initials: Z
authors.lastname: Song
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000475:Alkenes; D011714:Pyrans; D014297:Trimethylsilyl Compounds; C419804:trimethylsilyl iodide