Intramolecular Etherification and Polyene Cyclization of π-Activated Alcohols Promoted by Hot Water

作者：Fengzhi Zhang, Yan Tian, Guo‐Xing Li, Jin Qu · 发表于：The Journal of Organic Chemistry · 年份：2014 · DOI：10.1021/jo502636d · 被引用次数：69 · 研究领域：Synthesis of heterocyclic compounds、Organic and Inorganic Chemical Reactions、Synthesis and Catalytic Reactions

Hot water, acting as a mildly acidic catalyst, efficiently promoted intramolecular direct nucleophilic substitution reactions of unsaturated alcohols with heteroatom or carbon nucleophiles. In a mixed solvent of water and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), polyene cyclizations using allylic alcohols as initiators gave the desired cyclized products, and in neat HFIP, a tricyclization reaction gave a tetracyclic product in 51% chemical yield.