Phosphine-Catalyzed Enantioselective [1+4] Annulation
Asymmetric catalysis for chiral 2-pyrroline synthesis (Mar 2018 – Sep 2018)
| Advisor: Prof. Pengfei Li | Published: Asian Journal of Organic Chemistry 2019 (Co-first Author) |
Developed an enantioselective phosphine-catalyzed [1+4] annulation methodology for the synthesis of chiral 2-pyrrolines from Morita-Baylis-Hillman (MBH) carbonates and α,β-unsaturated imines.
Key Contributions
- Established an organic methodology using phosphine catalyst for [4+1] cycloaddition of unsaturated imine and MBH ester with a wide range of substituent groups
- Obtained chiral 2-pyrrolines with high yields and good enantioselectivities
- Proficient use of glove box for synthesis, column chromatography for purification, and HPLC/NMR for product characterization
Publication & Patent
- Qian, C.*; Zhang, P.*; Li, W.; Li, P. Phosphine Catalyzed Enantioselective [1+4]-Annulation of Morita-Baylis-Hillman Carbonates with α,β-Unsaturated Imines. Asian J. Org. Chem. 2019, 8 (2), 242–245. (*equal contribution)
- Li, P.; Qian, C.; Zhang, P. Method for efficient synthesis of optically active 2-pyrroline compound with catalysis of asymmetric organic phosphine. China National Patent, CN 201811539457.4.