Electron-Deficient Alkynes as Dipolarophile in Pd-Catalyzed Enantioselective (3 + 2) Cycloaddition Reaction with Vinyl Cyclopropanes

• DOI: 10.1021/acs.orglett.9b02431
• Publication Date: 2019-08-13T13:01:51Z
• Authors: Wen-Ping Ding; Gao-Peng Zhang; Yang-Jie Jiang; Juan Du; Xiu-Yan Liu; Di Chen; Chang-Hua Ding; Qing-Hai Deng; Xue-Long Hou
• Keywords: 01 natural sciences; 0104 chemical sciences

The activated alkynes have been used successfully for the first time as the dipolarophile in the palladium-catalyzed asymmetric (3 + 2) cycloaddition, affording highly functionalized cyclopentenes in good to high yields with high chemoselectivities and good to high enantioselectivities. The introduction of an additional carbonyl group at the α-position of the alkynyl esters is the key to activating the carbon-carbon triple bond. The reaction process was investigated, and an inverse process of Pd-catalyzed (3 + 2) cycloaddition was observed.