Rh(III)-Catalyzed Difunctionalization and

Contra-Thermodynamic Enantioselective Isomerization of Alkenes

Abstract: 

Alkenes  are  ubiquitous  functional  groups  in  numerous organic  molecules. Although significant  progress  has  been  made  in  the stereoselective synthesis  of alkenes and  their interconversions into other functional groups, the development of new and efficient synthetic transformation converting alkenes into valuable products is still of great interest. 

In the first part of the talk, I will present my Ph.D. works utilizing Rh(III) catalysis to develop unique and efficient synthetic strategies that give rapid access to biologically essential nitrogen- containing products from readily available alkenes.^1-3 

In the second part of the talk, I will introduce light-driven contra-thermodynamic catalysis 

that converts thermodynamically more stable internal alkenes into less stable terminal alkenes in a redox-neutral, catalytic, and asymmetric fashion using photoredox & Cr dual catalysis.^4-5

(1)   Lee, S.; Lei, H.; Rovis, T*. A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources. J. Am. Chem. Soc. 2019, 141, 12536. 

(2) Lee, S.;  Semakul,  N.;  Rovis, T*.  Direct  Regio- and  Diastereoselective  Synthesis  of  δ-Lactams  from Acrylamides and Unactivated Alkenes Initiated by Rh(III)-Catalyzed C-H Activation. Angew. Chem. Int. Ed. 2020, 59, 4965. 

(3)   Lee, S.; Rovis, T*. Rh(III)-Catalyzed Three-Component Syn-Carboamination of Alkenes Using Arylboronic Acids and Dioxazolones. ACS Catalysis 2021, 11, 8585. 

(4)   Lee, S.; Xu, E. Y.; Knowles, R. R*. 2023, Manuscript in preparation. 

(5)   Lee, S.; Lin, A.; Knowles, R. R*. 2023, Acc. Chem. Res. Manuscript in preparation.

20231019_대학원세미나_이수민 교수.pdf