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Simple Tandem Olefin Isomerization/Intramolecular Hydroamination of Alkenyl Amines with Various Allylic Tethers

Young Ho Kim, Dong Bin Kim and So Won Youn*

*Center for New Directions in Organic Synthesis, Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 04763, Korea, Email: sowony73hanyang.ac.kr

Y. H. Kim, D. B. Kim, S. W. Youn, J. Org. Chem., 2022, 87, 11919-11924.

DOI: 10.1021/acs.joc.2c01640


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Abstract

An operationally simple and efficient AgOTf-promoted tandem olefin isomerization/intramolecular hydroamination of 1,1-disubstituted alkenyl amines provides diverse 2-alkyl-substituted 1,3-X,N-heterocycles in very good yields through chemo- and regioselective C(sp3)-N bond formation with high atom economy. The reaction offers high functional group tolerance and broad substrate scope.

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proposed mechanism



General Procedure for AgOTf-Promoted Tandem Olefin Isomerization/Hydroamination

Substrate (0.189 - 3.171 mmol, 1 equiv) and AgOTf (2 - 20 mol%) were dissolved in ClCH2CH2Cl (1.9~31.7 ml, 0.1 M). The resulting mixture was stirred at 80 - 120 C for the reported time under aerobic conditions (in a closed vial with a screw cap). After the reaction was completed, the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc : n-Hexane = 1:3, 1:5, 1:6, 1:8, or 1:10) to give the corresponding product. All reactions were carried out 2-3 times repetitively and the average values of yields are given.


Key Words

benzo-fused N-heterocycles, benzo-fused O-heterocycles, benzo-fused S-heterocycles, oxazolidines


ID: J42-Y2022