1583276-18-9

Upstream product

• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 611-70-1 phenyl isopropyl ketone 
• 1403477-89-3 (4E)-2,2-dimethyl-1,5-diphenylpent-4-en-1-one oxime 
• 87562-50-3 (4E)-2,2-dimethyl-5-phenylpent-4-enenitrile 
• 4392-24-9 Cinnamyl bromide 
• 1431561-40-8 (1E, 4E)-2,2-dimethyl-5-phenylpent-4-enal oxime 
• 260352-12-3 (E)-5-(4-chlorophenyl)-2,2-diphenylpent-4-enal 

Relevant academic research and scientific papers

Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development

The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.

Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones

A method based on hydroamination mediated by inorganic base was developed for the synthesis of cyclic nitrones from alkenyl oximes. DFT calculations of the reaction pathway suggested that this hydroamination could proceed through an unprecedented nucleophilic amination of the unactivated alkene by the oxime nitrogen atom. The transition state of this reaction is stabilized by an ionic interaction between a metal cation such as K+ and the oxime oxygen and negatively charged alkene moiety. Basic ring building: A method for the synthesis of cyclic nitrones by using alkenyl oximes was developed based on hydroamination mediated by an inorganic base. DFT calculations for the reaction pathway suggested that this hydroamination could proceed through nucleophilic amination of the unactivated alkene by the oxime nitrogen atom, with the transition state stabilized by ionic interaction with a metal cation such as K+. Copyright