Mijin Jeon

Site-selective Cp*Rh(III)-catalyzed C–H amination of indolines with anthranils

The pyrimidinyl-directed C–H functionalization of indolines with anthranils as amination sources under rhodium(III) catalysis is described. This transformation efficiently provides a range of C7-aminated indoline derivatives with excellent site-selectivity and functional group compatibility. The resulting framework containing amino and carbonyl groups provides facile access to an important synthetic building block, which can be readily converted to biologically interesting heterocycles.

Trifluoromethylallylation of Heterocyclic C–H Bonds with Allylic Carbonates under Rhodium Catalysis

The rhodium(III)-catalyzed γ-trifluoromethylallylation of various heterocyclic C-H bonds with CF3-substituted allylic carbonates is described. These reactions provide direct access to linear CF3-containing allyl frameworks with complete trans-selectivity via C-H bond activation followed by a formal SN-type reaction pathway.

CCDC 1556654: Experimental Crystal Structure Determination

Related Article: Hyunjung Oh, Jihye Park, Sang Hoon Han, Neeraj Kumar Mishra, Suk Hun Lee, Yongguk Oh, Mijin Jeon, Gyeong-Joo Seong, Ka Young Chung, In Su Kima|2017|Tetrahedron|73|4739|doi:10.1016/j.tet.2017.06.052

Total Synthesis and Anti-inflammatory Evaluation of Penchinone A and Its Structural Analogues

The first total synthesis and biological evaluation of penchinone A and its structural analogues are described. The key steps for the preparation of penchinone A derivatives involve the oxime-directed palladium(II)-catalyzed oxidative acylation, Claisen rearrangement, and base-mediated olefin migration. This transformation efficiently provides a range of allyl-substituted biaryl ketones with site-selectivity and functional group compatibility. In addition, all synthetic compounds were screened for anti-inflammatory activity against nitric oxide (NO), tumor necrosis factor alpha (TNF-α), and interleukin-6 (IL-6) with lipopolysaccharide (LPS)-induced RAW264.7 cells. Generally, a range of penchinone A derivatives potently inhibited NO, TNF-α, and IL-6 productions, compared to dexamethasone as a positive control. Notably, penchinone A (8g) and its derivatives (8e and 8f) were found to exhibit anti-inflammatory activity stronger than that of dexamethasone.