20416-11-9Relevant academic research and scientific papers
Radical-Based C?C Bond-Forming Processes Enabled by the Photoexcitation of 4-Alkyl-1,4-dihydropyridines
Buzzetti, Luca,Prieto, Alexis,Roy, Sudipta Raha,Melchiorre, Paolo
supporting information, p. 15039 - 15043 (2017/11/20)
We report herein that 4-alkyl-1,4-dihydropyridines (alkyl-DHPs) can directly reach an electronically excited state upon light absorption and trigger the generation of C(sp3)-centered radicals without the need for an external photocatalyst. Selective excitation with a violet-light-emitting diode turns alkyl-DHPs into strong reducing agents that can activate reagents through single-electron transfer manifolds while undergoing homolytic cleavage to generate radicals. We used this photochemical dual-reactivity profile to trigger radical-based carbon–carbon bond-forming processes, including nickel-catalyzed cross-coupling reactions.
Forging Fluorine-Containing Quaternary Stereocenters by a Light-Driven Organocatalytic Aldol Desymmetrization Process
Cuadros, Sara,Dell'Amico, Luca,Melchiorre, Paolo
supporting information, p. 11875 - 11879 (2017/09/20)
Reported herein is a light-triggered organocatalytic strategy for the desymmetrization of achiral 2-fluoro-substituted cyclopentane-1,3-diketones. The chemistry is based on an intermolecular aldol reaction of photochemically generated hydroxy-o-quinodimethanes and simultaneously forges two adjacent fully substituted carbon stereocenters, with one bearing a stereogenic carbon–fluorine unit. The method uses readily available substrates, a simple chiral organocatalyst, and mild reaction conditions to afford an array of highly functionalized chiral 2-fluoro-3-hydroxycyclopentanones.
Cooperative activation with chiral nucleophilic catalysts and n-haloimides: Enantioselective iodolactonization of 4-arylmethyl-4-pentenoic acids
Nakatsuji, Hidefumi,Sawamura, Yasuhiro,Sakakura, Akira,Ishihara, Kazuaki
supporting information, p. 6974 - 6977 (2014/07/08)
Chiral triaryl phosphates promote the enantioselective iodolactonization of 4-substituted 4-pentenoic acids to give the corresponding iodolactones in high yields with high enantioselectivity. N-Chlorophthalimide (NCP) is employed as a Lewis acidic activat
Tin(IV) triflimidate-catalyzed cyclization of epoxy esters to functionalized δ-hydroxy-γ-lactones
Antoniotti, Sylvain,Du?ach, Elisabet
scheme or table, p. 2536 - 2539 (2009/07/26)
In the presence of 5 mol % of tin(IV) triflimidate, a cyclization reaction of epoxyesters to δ-hydroxy-γ-lactones proceeding in 46-98% yields without additives, ligands, or co-catalysts was observed. The cyclization to five-membered rings is greatly favor
Reactivity of Pyrrole Pigments. Part VII Autoxidation of Model Compounds for 5(2H)-Dipyrrylmethanones and 3,4-Dihydro-5(1H)-Pyrromethenones
Ribo, Josep M.,Serra, Xavier
, p. 185 - 200 (2007/10/02)
The autoxidation in alkine media and in the dark of some 5-methyl substituted 3,4-dimethyl-3-pyrrolin-2-ones and 5-methylene substituted pyrrolin-2-ones is studied.Both types of compounds are found to give autoxidation products that indicate very characteristic reaction pathways. - Keywords: Autoxidation; Bile pigments; Dihydropyrromethenoes; Dipyrrylmethanones
