Cyclization Of Enolate Research Articles

Catalyst‐Free Preparation of Perfluoroalkyl‐Phosphoryl Substituted Furans from 1‐Perfluoroalkyl 1,3‐Diketones in Two Steps

AbstractA two‐step catalyst‐free procedure for the construction of 3‐perfluoroalkyl‐2‐(phosphoryl)methyl furans from commercially available 1‐perfluoroalkyl 1,3‐diketones is reported. Propargylic alcohols, prepared by direct alkynylation of the diketones, react with PCl3 via [2,3]‐sigmatropic rearrangement – enolate cyclization sequence, leading to multifunctional furans. The reaction mechanism is supported by DFT study. In addition, the bioactivity modifying effect of phosphoryl group on 3‐perfluoroalkyl furans is depicted.magnified image

ChemInform Abstract: Synthesis of Phenanthrone Derivatives from sec‐Alkyl Aryl Ketones and Aryl Halides via a Palladium‐Catalyzed Dual C—H Bond Activation and Enolate Cyclization.

A palladium-catalyzed chelation-assisted C−H activation of alkyl aryl ketones and their reaction with aryl iodides to afford ortho-arylated products is described. For sec-alkyl aryl ketones, the catalytic reaction proceeds further to give 10,10-dialkylphenanthrone derivatives. A possible reaction mechanism involving directed dual C−H bond activation and enolate cyclization for the formation of 10,10-dialkylphenanthrone derivatives is proposed.

Synthesis of Phenanthrone Derivatives from sec-Alkyl Aryl Ketones and Aryl Halides via a Palladium-Catalyzed Dual C−H Bond Activation and Enolate Cyclization

A palladium-catalyzed chelation-assisted C-H activation of alkyl aryl ketones and their reaction with aryl iodides to afford ortho-arylated products is described. For sec-alkyl aryl ketones, the catalytic reaction proceeds further to give 10,10-dialkylphenanthrone derivatives. A possible reaction mechanism involving directed dual C-H bond activation and enolate cyclization for the formation of 10,10-dialkylphenanthrone derivatives is proposed.

Asymmetric synthesis of 3-alkyl substituted prolines by alkylation of a chiral sulfone

Preparation of 3-alkyl substituted prolines was achieved by alkylation of a chiral sulfone obtained from the amino–zinca-ene–enolate cyclization.