School of Chemistry and Materials Science, the Key Laboratory of Biotechnology for Medicinal Plants of Jiangsu Province, Jiangsu Normal University, Xuzhou, 221116, China.
Department of Geriatrics, the First Affiliated Hospital of Nanjing Medical University, Nanjing, 210029, China.
Org Biomol Chem. 2020 Jul 22;18(28):5388-5399. doi: 10.1039/d0ob01049a.
A catalytic asymmetric (4 + 2) cyclization of ortho-hydroxyphenyl-substituted para-quinone methide derivatives with 3-vinylindoles has been established in the presence of chiral phosphoric acid, which provides a series of chiral chroman derivatives bearing an indole moiety in generally high yields (up to 97%), and with good enantioselectivities (up to 90% ee) and moderate to good diastereoselectivities (up to 95 : 5 dr). This reaction has not only fulfilled the need of developing catalytic asymmetric (4 + 2) cyclizations of para-quinone methide derivatives with electron-rich alkenes, but also provided a useful method for constructing chiral chroman scaffolds.
在手性磷酸的存在下，建立了邻羟基苯基取代的对醌甲川衍生物与 3-乙烯基吲哚的催化不对称（4+2）环化反应，该反应以一般高收率（高达 97%）和良好的对映选择性（高达 90%ee）和中等至良好的非对映选择性（高达 95：5 dr）提供了一系列带有吲哚部分的手性色满衍生物。该反应不仅满足了开发富电子烯烃与对醌甲川衍生物的催化不对称（4+2）环化的需求，而且为构建手性色满支架提供了一种有用的方法。
