588717-74-2Relevant academic research and scientific papers
A novel class of bidentate ligands with a conformationally flexible biphenyl unit built into a planar chiral [2.2]paracyclophane backbone
Rozenberg,Antonov,Zhuravsky,Vorontsov,Starikova
, p. 3801 - 3804 (2003)
We report the synthesis of a novel class of planar chiral bidentate aryl[2.2]paracyclophane ligands. For the first time in the [2.2]paracyclophanyl series the Pd-catalyzed Suzuki cross-coupling was employed for the formation of the arylparacyclophanyl skeleton. From the two possible approaches: (a) cross-coupling of [2.2]paracyalophanylboronic acids with aryl halides; (b) cross-coupling of [2.2]paracyclophanyl halides with arylboronic acids, the latter was found to be more efficient. This approach was successfully used for the synthesis of a wide range of aryl[2.2]paracyclophanes with different types of substitution patterns (ortho-, pseudo-ortho- or pseudo-gem-arrangement of the functionally-substituted aryl fragment with respect to the substituent in the paracyclophane ring).
Aryl[2.2]paracyclophane-based chiral regioisomeric analogs of salicyl aldehyde: Novel sources for construction of phenoxy-imine ligands
Zhuravsky, Roman P.,Danilova, Tatiana I.,Antonov, Dmitrii Yu.,Sergeeva, Elena V.,Starikova, Zoya A.,Godovikov, Ivan A.,Il'In, Michail M.,Rozenberg, Valeria I.
experimental part, p. 156 - 170 (2012/05/20)
The efficient, high-yield approaches to two novel regioisomeric salicyl aldehyde analogs, 4-formyl-13-(2-hydroxyphenyl)-[2.2]paracyclophane and 4-formyl-12-(2-hydroxyphenyl)-[2.2]paracyclophane (iso-FHPhPC and pseudo-FHPhPC, respectively), constructed on the basis of an aryl[2.2]paracyclophane backbone are described. The key stage of the backbone formation is the Suzuki cross-coupling of paracyclophanyl halides with arylboronic acids. Efficient procedures for the resolution of the racemic hydroxy aldehydes into enantiomers via Schiff bases with enantiomers of α-phenylethyl amine were elaborated, and the absolute configurations of enantiomers were established on the basis of X-ray analysis of diastereomeric imines. Starting from these chiral hydroxy aldehydes the first representatives of bi-, tri-, and tetradentate phenoxy-imine ligands belonging to an aryl[2.2]paracyclophane family were obtained. The induction power of the ligands was tested in the Et2Zn asymmetric addition to aldehydes. Copyright
