Abstract
A strategic approach to incorporate CF3 group into oxindoles, pyrrolidines, and isoxazolones to construct spiro heterocyclic skeletons with quaternary carbon stereocenters was developed. Using a DMAP catalyst under mild conditions, the controllable synthesis of spiro oxindole-pyrrolidine-isoxazoline derivatives was achieved via concerted 1,3-dipolar cycloaddition reactions of arylidene isoxazolones with N-(2,2,2-trifluoroethyl)isatin ketimines. This method exhibits robust regioselectivity and provides a series of isoxazolone-based bispiro heterocycles in good to high yields (72 %–99 %) with excellent diastereoselectivity (in all cases >20 : 1 dr), offering new candidate compounds for drug screen.
Original language | English |
---|---|
Article number | e202400959 |
Journal | European Journal of Organic Chemistry |
Volume | 27 |
Issue number | 48 |
DOIs | |
Publication status | Published - 23 Dec 2024 |
Keywords
- 1,3-dipolar cycloaddition
- Isatin ketimines
- Isoxazolones
- Oxindoles
- Spiroheterocycles