148433-41-4

Upstream product

• 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.

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 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

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