Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)₃/LiI system as the promoter

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• 作者：Thibaut Chalopin^a ; Khaoula Jebali^a ; ^c ; Catherine Gaulon-Nourry^b ; Fabrice Dé ; nè ; s^a ; Jacques Lebreton^a ; Monique Mathé ; -Allainmat^a ; ^{monique.mathe@univ-nantes.fr" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Oxygen heterocycles ; Prins cyclization ; Lewis acid ; Elimination ; Regioselectivity
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：14 January 2016
• 年：2016
• 卷：72
• 期：2
• 页码：318-327
• 全文大小：607 K

文摘

The rapid and regioselective synthesis of a series of 2,6-disubstituted dihydropyranic building-blocks bearing an oxygenated side chain is described. The corresponding 4-iodo tetrahydropyran precursors, easily prepared by Prins cyclization, underwent regioselective elimination in the presence of an In(OAc)₃/LiI system to provide the title compounds. The one-pot Prins cyclization-elimination process was also studied and could be achieved with the TMSBr/LiI/In(OAc)₃ system.