Catalytic asymmetric amination of azlactones with azobenzenes

Abstract

We reported an efficient asymmetric amination of azlactones with N-aryl-N-aroyldiazenes through a chiral N,Nʹ-dioxide-based Lewis acid catalyst. The multicoordination ability of Nd(III) enabled it to simutaneously activate and to locate...

Asymmetric synthesis of cyclopenta[b]indoles via organocatalytic formal (3 + 2) cyclization of β-keto ester with azonaphthalene

“…N -Aryl- N -carbonyldiazenes are useful building blocks in synthetic chemistry due to the fact that the azo unit is a fine functional group and a directing group. 1 In comparison with azobenzenes, 2 azonaphthalenes participate in the transformation with better reactivity and selectivity, which has been extensively developed in recent years. The enantioselective formal ortho -CH bond nucleophilic aromatic substitution, developed by Tan's group and others, enabled the construction of axial chiral biaryls connected with a carbon–carbon or carbon–heteroatom bond, 3 of which the other aryl partners involved 2-substituted indoles, 4 arylboronic acids, 5 pyrazolone, 6 2-naphthol or 2-naphthylamine, 7 carbazole, 8 and phenoxazine 9 as well.…”