189008-33-1Relevant articles and documents
Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds
Wu, Wei,Liao, Na,Wei, Qi,Huang, Jiaying,Huang, Qi,Peng, Yungui
supporting information, p. 6872 - 6876 (2021/09/14)
An efficient asymmetric tandem reaction of o-alkynylbenzaldehydes, amines, and diazo compounds catalyzed by chiral silver imidodiphosphate has been established. Chiral 1,2-dihydroisoquinoline analogues have a tertiary stereocenter at the C1 position, and substituents at the C3 position are available with up to 97% yields and 98% ee. These products can be elaborated into the corresponding β-aminophosphonates or PARP1-inhibitor analogues.
Light-Enabled Radical 1,4-Aryl Migration Via a Phospho-Smiles Rearrangement
De Abreu, Maxime,Belmont, Philippe,Brachet, Etienne
, p. 3758 - 3767 (2021/02/01)
Rearrangement reactions in organic chemistry are attractive strategies to build efficiently complex scaffolds, in just one step, from simple starting materials. Among them, aryl migrations are certainly one of the most useful and straightforward rearrangement for building attractive carbon-carbon bonds. Of note, anionic aryl migration reactions have been largely described compared to their radical counterparts. Recently, visible-light catalysis has proven its efficiency to generate such radical rearrangements due to the concomitant loss of a particle (often CO2 or SO2), which is the driving-force of the reaction. Here, we disclose a Smiles-type rearrangement, triggered by a phosphorus-containing unit (arylphosphoramidate), therefore called "phospho-Smiles"rearrangement, allowing a Csp2-Csp2 bond formation thanks to a 1,4-aryl migration reaction. In addition, combining this approach with a radical hydroamination/amination reaction produces an amination/phospho-Smiles cascade particularly attractive, for instance, to investigate the synthesis of the phthalazine core, a scarcely described scaffold of interest for medicinal chemistry projects.
Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds
Li, Quanzhe,Liu, Ruixing,Wei, Yin,Shi, Min
supporting information, p. 2664 - 2669 (2021/04/05)
Employing silver/rhodium relay catalysis strategy, an intramolecular electrophilic cyclization and C?H activation followed by cascade hydrogenation and reductive amination has been developed. The acylmethylated isoquinoline derivatives could be afforded with broad substrate scope in 23–88% yields, which could be further transformed to the core skeleton of hexahydrodibenzo[a,g]quinolizine as drug-candidates. Moreover, this reaction was achieved in a gram-scale. A reasonable reaction mechanism has been proposed based on a series of control and KIE experiments. (Figure presented.).
