Reversal of diastereoselectivity in palladium-arene interaction directed hydrogenative desymmetrization of 1,3-diketones
Tóm tắt
For the metal-catalyzed asymmetric hydrogenation of α-substituted ketones, cis reductive products are generally obtained due to steric hindrance of substituents. Herein, an unprecedented trans reductive products were observed in palladium-catalyzed hydrogenative desymmetrization of cyclic and acyclic 1,3-diketones, providing the chiral trans β-hydroxy ketones with two adjacent stereocenters including one α-tertiary or quaternary stereocenter with high enantioselectivity and diastereoselectivity. Mechanistic studies and DFT calculations suggested that the rarely observed diastereoselectivity reversal is ascribed to the charge-charge interaction between the palladium and aromatic ring of the substrate, which could not only result in the reversal of the diastereoselectivity, but also improve the reactivity.
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The summed interaction between the active Pd-H and phenyl/methyl also evaluated. See details in Supporting Information.
During our preparation of this manuscript, a related irdium-catalyzed hydrogenative desymmetrization of 1,3-diketones was reported by Zhang’s group, please see: The chiral Ir/f-ampha complex catalyst was used, and cis product was obtained. In our work, trans products were observed.. Gong Q, Wen J, Zhang X. Chem Sci, 2019, 10: 6350–6353