21277-39-4Relevant academic research and scientific papers
Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer
Miller, David C.,Choi, Gilbert J.,Orbe, Hudson S.,Knowles, Robert R.
, p. 13492 - 13495 (2015/11/09)
Here we report a ternary catalyst system for the intramolecular hydroamidation of unactivated olefins using simple N-aryl amide derivatives. Amide activation in these reactions occurs via concerted proton-coupled electron transfer (PCET) mediated by an excited state iridium complex and weak phosphate base to furnish a reactive amidyl radical that readily adds to pendant alkenes. A series of H-atom, electron, and proton transfer events with a thiophenol cocatalyst furnish the product and regenerate the active forms of the photocatalyst and base. Mechanistic studies indicate that the amide substrate can be selectively homolyzed via PCET in the presence of the thiophenol, despite a large difference in bond dissociation free energies between these functional groups.
Asymmetric Diels-Alder Reaction Using (S)-Pyroglutamic Acid Derivatives as Chiral Dienophiles
Ikota, Nobuo
, p. 2219 - 2221 (2007/10/02)
Asymmetric Diels-Alder reaction of cyclopentadiene with chiral dienophiles (3) derived from (S)-pyroglutamic acid derivatives was performed in the presence of a Lewis acid such as diethylaluminium chloride in toluene to afford the cycloadducts with high diastereoselectivity.Keywords asymmetric reaction; Diels-Alder reaction; (S)-pyroglutamic acid; chiral dienophile; diethylaluminium chloride; (2+4)cycloaddition
