An article Reversal of diastereoselectivity in palladium-arene interaction directed hydrogenative desymmetrization of 1,3-diketones WOS:000492586400002 published article about CATALYZED ASYMMETRIC HYDROGENATION; MOLECULAR-STRUCTURE; COORDINATION; COMPLEXES; PHOSPHORAMIDITE; DERIVATIVES; COMPOUND; LIGANDS; KETONES; ACIDS in [Yu, Chang-Bin; Wang, Heng-Ding; Song, Bo; Shen, Hong-Qiang; Fan, Hong-Jun; Zhou, Yong-Gui] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China; [Wang, Heng-Ding] Univ Chinese Acad Sci, Beijing 100049, Peoples R China in 2020, Cited 57. Category: benzofurans. The Name is Isobenzofuran-1(3H)-one. Through research, I have a further understanding and discovery of 87-41-2
For the metal-catalyzed asymmetric hydrogenation of alpha-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 beta-hydroxy ketones with two adjacent stereocenters including one alpha-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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Reference:
Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem