Formal [5+3] Cycloaddition of Vinylethylene Carbonates with Isatin‐Based α‐(Trifluoromethyl)imines for Diastereoselective Synthesis of Medium‐Heterocycle‐Fused Spirooxindoles. Issue 20 (2nd September 2019)

• Record Type: Journal Article
• Authors: Zhao, Hong‐Wu; Wang, Li‐Ru; Guo, Jia‐Ming; Ding, Wan‐Qiu; Song, Xiu‐Qing; Wu, Hui‐Hui; Tang, Zhe; Fan, Xiao‐Zu; Bi, Xiao‐Fan
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 20(2019)
• Page Start: 4761
• Page End: 4771
• Publication Date: 2019-09-02
• Subjects: [5+3] cycloaddition -- vinylethylene carbonate -- isatin-based α-(trifluoromethyl)imine -- spirooxindole; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900651
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: In the presence of Pd(PPh3 )4 (2.5 mol%), PPh3 (10 mol%) and pyridine (2.0 equiv.), the formal [5+3] cycloaddition of vinylethylene carbonates with isatin‐based α‐(trifluoromethyl)imines proceeded readily, and delivered trans ‐configured novelmedium‐heterocycle‐fused spirooxindoles in 75–97% chemical yields with excellent diastereoselectivities. The relative stereochemical configuration of the title products was identified by X‐ray diffraction analysis. Abstract :