Catalytic Asymmetric [4+2] Cyclization of para-Quinone Methide Derivatives with 3-Alkyl-2-vinylindoles
Catalytic Asymmetric [4+2] Cyclization of para-Quinone Methide Derivatives with 3-Alkyl-2-vinylindoles
复制标题
对醌甲基化物衍生物与 3-烷基-2-乙烯基吲哚的催化不对称 [4 2] 环化
DOI：
10.1002/adsc.201800829
复制
发表时间：
2018-11-05
影响因子：
5.4
通讯作者：
Shi, Feng
中科院分区：
文献类型：
--
作者：
Jiang, Xiao-Li;Wu, Shu-Fang;Shi, Feng
在手性磷酸存在下，对苯醌甲基化物（p-QM）与3-烷基-2-乙烯基吲哚的催化不对称[4+2]环化反应得到了手性苯并二氢吡喃骨架，产率高达98%，非对映选择性高达95：5dr，对映选择性高达96% ee.该反应首次实现了p-QM衍生物与富电子烯烃的催化不对称[4+2]环化反应，丰富了p-QM衍生物催化不对称反应的研究领域.此外，该催化不对称环化反应还成功地应用于3-烷基-2-乙烯基吲哚的环化反应。更重要的是，该反应将为构建对映体富集的色满骨架提供一种有用的方法。
A catalytic asymmetric [4+2] cyclization of para-quinone methide (p-QM) derivatives with 3-alkyl-2-vinylindoles in the presence of a chiral phosphoric acid has been established, and this method provides chiral chroman frameworks in good yields (up to 98%) with high diastereoselectivities (up to >95:5 dr) and excellent enantioselectivities (up to 96% ee). This reaction represents the first catalytic asymmetric [4+2] cyclization of p-QM derivatives with electron-rich alkenes, which will enrich the field of catalytic asymmetric reactions of p-QM derivatives. In addition, this catalytic asymmetric cyclization was successfully applied to 3-alkyl-2-vinylindoles. More importantly, this reaction will offer a useful method for the construction of enantioenriched chroman frameworks.