65007-15-0

Upstream product

• 4916-74-9 (3,5-dimethylcyclopenta-2,5-diene-1,2-diyl)dibenzene 
• 106-51-4 p-benzoquinone 
• 5141-37-7 2,5-Dimethyl-3,4-diphenyl-cyclopent-2-en-1-ol 
• 16643-55-3 2,5-dimethyl-3,4-diphenyl-2-cyclopentene-1-one 
• 5141-38-8 2,5-Dimethyl-3,4-diphenyl-cyclopent-2-en-1,4-diol 
• 5423-06-3 4-hydroxy-2,5-dimethyl-3,4-diphenylcyclopent-2-enone 
• 134-81-6 benzil 

Relevant academic research and scientific papers

Catalytic Enantioselective Desymmetrization of Norbornenoquinones via C(sp2)-H Alkylation

The enantioselective Diels-Alder (DA) reaction with monosubstituted p-benzoquinones is an unmet challenge. A new approach for the enantioselective synthesis of monosubstituted quinone-DA adducts is presented based on C(sp2)-H alkylative desymmetrization of meso-DA adducts. Catalyzed by a tertiary amino-thiourea derivative, this reaction utilizes nitroalkanes as the alkylating agents and generates densely functionalized products bearing at least four contiguous stereogenic centers remote from the reaction site with excellent enantioselectivities.

Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck

Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.