Gold(I)-Catalyzed Angle Strain Controlled Strategy to Furopyran Derivatives from Propargyl Vinyl Ethers: Insight into the Regioselectivity of Cycloisomerization
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- 作者：Shengfei Jin ; Chongguo Jiang ; Xiaoshi Peng ; Chunhui Shan ; Shanshan Cui ; Yuanyuan Niu ; Yang Liu ; Yu Lan ; Yongxiang Liu ; Maosheng Cheng
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：February 19, 2016
- 年：2016
- 卷：18
- 期：4
- 页码：680-683
- 全文大小：414K
- ISSN：1523-7052
文摘
A unique strategy for the regiospecific synthesis of bicyclic furopyran derivatives has been developed via a gold(I)-catalyzed propargyl-Claisen rearrangement/6-endo-trig cyclization of propargyl vinyl ethers. The introduction of angle strain into the substrates significantly altered the reaction’s regioselectivity. Insight into the regioselectivity of the cycloisomerization was obtained with density functional theory calculations.