Chirality-Sensing Supramolecular Systems

Chiral differentiation of some cyclopentane and cyclohexane β-amino acid enantiomers through ion/molecule reactions

“…Chiral crown ether derivatives and ␤-cyclodextrin ( Figure 2) were selected because of their good ability to form host-guest complexes, as well as to recognize and differentiate enantiomers, especially using different chromatographic and mass spectrometric methods [11-17, 28 -35]. The same host compounds were used for both cyclopentane ␤-amino acids (1-4) and cyclohexane ␤-amino acids (5)(6)(7)(8).…”

Metalloporphyrin Symmetry in Chiral Recognition and Enantioselective Catalysis

“…Since the pioneering work of Cram [12] and Lehn [13] on the chiral recognition of amino esters and acids by binaphthyl hosts, several approaches to the design and preparation of new chiral hosts have been reported. Many studies have been focused on metalloporphyrins as chiral hosts, because these macrocycles are quite rigid and can provide multiple chiral recognition sites by various chemical modifications of the porphyrin ring [10]. Our efforts in this area have been largely directed toward the systematic investigation of the reactivity of chiral ruthenium porphyrins with racemic amino acids, phosphines and isocyanides [9].…”

“…Catalysis by metalloporphyrins is, however, not limited to the reactions that mimic the reactions catalyzed by the cytochrome P450 family, but can be extended to different processes, which should provide original methods for asymmetric organic syntheses. Thus, the design of chiral porphyrins as asymmetric catalysts and selective receptors of various substrates is of increasing interest in the development of enantioselective catalysis and chiral recognition [9,10]. Porphyrins possess a number of structural features that make them attractive for the stereocontrol of metal-catalyzed reactions [11].…”

Palladium-Catalyzed Polyfluorophenylation of Porphyrins with Bis(polyfluorophenyl)zinc Reagents

“…The construction of porphyrins and related tetrapyrrolic macrocycles has attracted much interest [1][2][3][4][5][6] because they have a variety of important applications in many fields [7,8], including catalysis [9][10][11][12][13][14], medicine [15][16][17][18], and materials [19][20][21][22][23][24][25][26][27]. It is also well documented that the chemical, physical, and biological properties of porphyrin macrocycles can be systematically tuned by the electronic, steric and conformational environments of their peripheral substituents [7,8].…”