Synthesis of functional meso-aryl porphomonomethenes and porphodimethenes: application to the preparation of a chiral calix[4]phyrin dimer.
Reaction of 5,5-dimethyldipyrromethane (1) with electron-deficient aryl aldehydes in the presence of BF(3)-Et(2)O and NH(4)Cl in propionitrile constitutes efficient, easy access to unprecedented, functional porphomonomethenes together with the expected porphodimethenes (calix[4]phyrins). Alternatively, when the reaction was carried out in CH(2)Cl(2) in the presence of an acid and Florisil, the expected bis-arylcalix[4]phyrin was isolated in 41% yield, while no scrambled macrocycle was detected. After reduction of the nitro function, porphomonomethene 9 was efficiently condensed with the binaphthyl diacyl chloride (10) leading to the first chiral calix[4]phyrin dimer (11) that exhibits a moderate enantiorecognition toward the enantiomers of malic acid.
Bernátková
Markéta
M
Laboratoire de Chimie Organique UMR 7611, Université P. et M. Curie, Tour 44-45, 1 étage, case 181, 4, Place Jussieu, 75252 Paris Cedex 05, France.
Andrioletti
Bruno
B
Král
Vladimír
V
Rose
Eric
E
Vaissermann
Jacqueline
J