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• 83-12-5 phenindione 

Relevant academic research and scientific papers

Reversal of diastereoselectivity in palladium-arene interaction directed hydrogenative desymmetrization of 1,3-diketones

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.

Method for synthesizing chiral beta-hydroxyketone by palladium-catalyzed asymmetric reduction

The invention provides a method for synthesizing chiral beta-hydroxyketone by palladium-catalyzed asymmetric reduction, which comprises the following steps: by using protons as a hydrogen source, obtaining chiral beta-hydroxyketones containing various sub

Diboron-mediated palladium-catalyzed asymmetric transfer hydrogenation using the proton of alcohols as hydrogen source

The developments of hydrogen sources stand at the forefront of asymmetric reduction. In contrast to the well-studied alcohols as hydrogen sources via β-hydride elimination, the direct utilization of the proton of alcohols as a hydrogen source for activator-mediated asymmetric reduction is rarely explored. Herein we report the proton of alcohols as a hydrogen source in diboron-mediated palladium-catalyzed asymmetric transfer hydrogenation of 1,3-diketones and indoles, providing a series of chiral β-hydroxy ketones and indolines with excellent yields and enantioselectivities. This strategy would be useful for the synthesis of chiral deuterium-labelled compounds due to the ready availability of deuterium-labelled alcohols. Mechanistic investigations and DFT calculations revealed that active chiral Pd-H species was generated from the proton of alcohols by activating of tetrahydroxydiboron, hydrogen transfer was the rate-determining step, and the reaction preferred Pd(0)-catalyzed mechanism. [Figure not available: see fulltext.]

Method for synthesizing beta-hydroxy ketone by palladium-catalyzed asymmetric hydrogenation of 1, 3-diketone

The invention relates to a method for synthesizing chiral beta-hydroxy ketone by palladium-catalyzed asymmetric hydrogenation of 1, 3-diketone. The method comprises the following steps: adding 10-100mol% of acid into 1-5mol% of a palladium catalyst, and c