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Synthesis and Spectral and Structural Characterization of a New Series of Bis‐Strapped Chiral Porphyrins Derived from L ‐Proline
Author(s) -
Boitrel Bernard,
BaveuxChambenoît Valérie,
Richard Philippe
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200111)2001:22<4213::aid-ejoc4213>3.0.co;2-p
Subject(s) - porphyrin , chemistry , atropisomer , linker , superstructure , enantioselective synthesis , stereochemistry , catalysis , crystallography , proline , crystal structure , combinatorial chemistry , photochemistry , organic chemistry , amino acid , biochemistry , oceanography , computer science , geology , operating system
New chiral porphyrins were obtained in reasonable yields in three steps, starting from the αβαβ atropisomer of meso ‐tetrakis( o ‐aminophenyl)porphyrin (TAPP). These potential catalysts for the enantioselective epoxidation of alkenes were obtained by the reaction of different linkers on the same L ‐prolinoyl‐picket porphyrin. Their 1 H NMR spectral characteristics, as well as the crystal structure of one of them, clearly indicate that the orientation of the proline cycle depends on the linker used to tether the two pickets on each side of the porphyrin. The same linker is employed for both sides of the porphyrin; hence the resulting D 2 ‐symmetric superstructure.