《Organocatalytic Atroposelective Synthesis of N-N Axially Chiral Indoles and Pyrroles by De Novo Ring Formation》 was written by Chen, Ke-Wei; Chen, Zhi-Han; Yang, Shuang; Wu, Shu-Fang; Zhang, Yu-Chen; Shi, Feng. Application of 30414-53-0 And the article was included in Angewandte Chemie, International Edition on April 19 ,2022. The article conveys some information:
The first highly atroposelective construction of N-N axially chiral indole scaffolds I [R = H, 4-F, 6-MeO, 7-Br, etc.; R1 = H, Me; R2 = CO2Me, CO2Et, Ph, etc.; R3 = Me, Et, i-Pr, Bn; R4 = Ph, 2-FC6H4, 3-FC6H4, etc.] was established via a new strategy of de novo ring formation. This strategy made use of the organocatalytic asym. Paal-Knorr reaction of well-designed N-aminoindoles with 1,4-diketones, thus affording N-pyrrolylindoles in high yields and with excellent atroposelectivities (up to 98% yield, 96% ee). In addition, this strategy was applicable for the atroposelective synthesis of N-N axially chiral bispyrroles II [R5 = Ph, 3-ClC6H4, 3-MeOC6H4, 1-naphthyl, 2-naphthyl; R6 = Me, Et, Bn; R7 = Me, Et, i-Pr; R8 = Ph, 2-FC6H4, 3-thienyl, etc.; R9 = Me, Et, i-Pr, Bn] (up to 98% yield, 97% ee). More importantly, such N-N axially chiral heterocycles could be converted into chiral organocatalysts with applications in asym. catalysis, and some mols. display potent anticancer activity. This work not only provided a new strategy for the atroposelective synthesis of N-N axially chiral mols. but also offers new members of the N-N atropisomer family with promising applications in synthetic and medicinal chem. In the part of experimental materials, we found many familiar compounds, such as Methyl 3-oxovalerate(cas: 30414-53-0Application of 30414-53-0)
Methyl 3-oxovalerate(cas: 30414-53-0) belongs to ketone compounds. They are most widely used as solvents, especially in industries manufacturing explosives, lacquers, paints, and textiles. Ketones are also used in tanning, as preservatives, and in hydraulic fluids.Application of 30414-53-0
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