State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering , Lanzhou University , Lanzhou 730000 , People's Republic of China.
Syngenta Jealott's Hill International Research Centre , Bracknell , Berks RG42 6EY , United Kingdom.
Org Lett. 2018 Apr 20;20(8):2190-2194. doi: 10.1021/acs.orglett.8b00503. Epub 2018 Mar 29.
An efficient method has been successfully developed to achieve the asymmetric C-H functionalization of indoles in the carbocyclic ring via organocatalysis, and a variety of tetrahydropyranoindoles were synthesized in good yields with excellent stereoselectivities. Further study on thermodynamic calculations indicated that the process was promoted by generating more thermodynamically stable products. This strategy, together with traditional C-3 functionalization of hydroxyindoles, could realize the switchable, regiodivergent asymmetric modification of indoles.
已成功开发出一种有效的方法，通过有机催化实现碳环中环吲哚的不对称 C-H 官能化，合成了多种四氢吡喃吲哚，产率高，立体选择性好。进一步的热力学计算研究表明，该过程是通过生成更热力学稳定的产物来促进的。该策略与传统的羟基吲哚的 C-3 官能化相结合，可以实现吲哚的可切换、区域发散的不对称修饰。
