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Palladium-Catalyzed Asymmetric Decarboxylative [4+2] Dipolar Cycloaddition of 4‑Vinyl-1,3-dioxan-2-ones with α,β-Disubstituted Nitroalkenes Enabled by a Benzylic Substituted P,N-Ligand

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journal contribution
posted on 26.06.2020, 19:04 by Juan Du, Yuan-Da Hua, Yang-Jie Jiang, Shuai Huang, Di Chen, Chang-Hua Ding, Xue-Long Hou
The Pd-catalyzed asymmetric [4+2] cycloaddition reaction of an aliphatic 1,4-dipole with singly activated electron-deficient alkenes is realized for the first time, enabled by using a newly developed benzylic substituted P,N-ligand, affording tetrahydropyrans having three continuous chiral centers in high yields with high diastereo- and enantioselectivities. The rational transition states of the reaction as well as the role of the benzylic chiral center are proposed.