143112-20-3Relevant academic research and scientific papers
Ruthenium(II)-Catalyzed Cyclization of Aromatic Acids with Allylic Acetates via Redox-Free Two-Fold Aromatic/Allylic C-H Activations: Combined Experimental and DFT Studies
Jambu, Subramanian,Tamizmani, Masilamani,Jeganmohan, Masilamani
, p. 1982 - 1986 (2018)
A Ru(II)-catalyzed, redox-free, two-fold aromatic/allylic C-H bond activation of aromatic acids with allylic acetates to give (Z)-3-ylidenephthalides is described. In the reaction, H2 was formed as a side product. The detailed mechanistic investigation and DFT studies including the transition-state analysis support the postulate that the C-H allylation takes place at the ortho position of aromatic acids with allylic acetates followed by intramolecular cyclization at the allylic C(sp3)-H via a π-allylruthenium intermediate.
Catalytic C-N and C-H Bond Activation: Ortho-Allylation of Benzoic Acids with Allyl Amines
Hu, Xiao-Qiang,Hu, Zhiyong,Zhang, Guodong,Sivendran, Nardana,Goo?en, Lukas J.
supporting information, p. 4337 - 4340 (2018/07/29)
A facile insertion of ruthenium into aromatic C-H and allylic C-N bonds are the key steps in a [Ru(p-cymene)Cl2]2-catalyzed ortho-C-H allylation of benzoic acids. This protocol allows drawing on the large pool of allylic amines for state-of-the-art ortho-functionalizations of arenes, turning neutral amines into leaving groups. Concise syntheses of biologically active compounds provide further evidence of the synthetic potential of this methodology.
7-Mesityl-2,2-dimethylindan-1-ol: A novel alcohol which serves as both a chiral auxiliary and a protective group for carboxy functions
Koshiishi, Eiji,Hattori, Tetsutaro,Ichihara, Naoki,Miyano, Sotaro
, p. 377 - 383 (2007/10/03)
A novel chiral indanol 11 is conveniently synthesized by using a stepwise displacement of the methoxy groups of 2,6-dimethoxybenzoic ester 1 by a vinyl and then an aryl Grignard reagent as the key step. The racemic indanol 11 is optically resolved as the diastereomeric (Sa)-2′-methoxy-1,1′-binaphthyl-2-carboxylic esters 12 by column chromatography. The absolute stereochemistry of the indanol (+)-11 is established to be S by an X-ray crystallographic analysis of the ester (Sa,S)-12. Performance of the indanol 11 as a chiral auxiliary, and as a protective group for the carboxy function, is examined in the atrolactic acid synthesis from phenylglyoxylic ester 13 and methylmagnesium iodide and in the biphenyl coupling reaction of 2,3-dimethoxybenzoic ester 15 with 2-methoxy-4,6-dimethylphenylmagnesium bromide, resulting in quantitative formations of atrolactic ester 14 with up to 83% de and biphenyl 16 with 72% de, respectively.
