Diels–Alder Reactions with Ethylene and Superelectrophiles

• DOI: 10.1021/acs.orglett.8b00367
• Publication Date: 2018-03-26T18:44:42Z
• Authors: Hien Vuong; Barada P. Dash; Sten O. Nilsson Lill; Douglas A. Klumpp
• Keywords: Diels–Alder reaction

Diels–Alder reactions have been accomplished with ethylene as the dienophile through use of inverse-electron demand chemistry. As a key aspect chemistry, dienes are part tri- or dicationic superelectrophilic systems. Theoretical calculations reveal that highly charged superelectrophiles possess exceptionally low lying LUMOs, and this facilitates cycloaddition chemistry ethylene. The has used to prepare series tetrahydroquinoline products. This represents first application activation in reaction, new method utilizing C2 building block.