Catalytic asymmetric dearomatization (CADA) reactions of phenol and aniline derivatives

Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives.

An intramolecular enantioselective metal-catalyzed dearomatization reaction is described. This procedure allows the dearomatization of naphthalene derivatives through an electrophilic aromatic substitution-type reaction on a Pd(II) intermediate. The high yields and enantioselectivities achieved make this procedure a valuable method for synthetic chemists.

Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.

An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N'-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the e...

Catalytic asymmetric conjugate addition/oxidative dearomatization towards multifunctional spirocyclic compounds.

Synthesis of nitrogen-containing fused-polycyclic compounds from tyramine derivatives using phenol dearomatization and cascade cyclization.

We developed a novel method of synthesizing nitrogen-containing fused-polycyclic compounds using tyramine derivatives as substrates. The method is based on the dearomatization of phenols via an intramolecular ipso-Friedel-Crafts allenylation and sequential bond-forming-cleavage reactions initiated by the construction of an indole skeleton. Structurally diverse fused-heterocycles were produced i...

Direct Catalytic Asymmetric Synthesis of Pyrazolidine Derivatives

The importance and increased demand of pharmaceutically active azaheterocycles has urged the development of inexpensive and environmentally benign catalytic asymmetric technologies. 2] In this context, the pyrazolidine and pyrazoline structural motif is present in several compounds with significant bioactivities, such as anti-inflammatory, antidepressant, anticancer, antibacterial and antiviral...