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Aryl[2.2]paracyclophane‐Based Chiral Regioisomeric Analogs of Salicyl Aldehyde: Novel Sources for Construction of Phenoxy‐Imine Ligands
Author(s) -
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.
Publication year - 2012
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201100096
Subject(s) - chemistry , imine , aldehyde , diastereomer , aryl , enantiomer , yield (engineering) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl , materials science , metallurgy
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 Et 2 Zn asymmetric addition to aldehydes.