Synthesis and enantiomeric recognition ability of 22-crown-6 ethers derived from rosin acid and BINOL

Chiral Cryptands Possessing Tetraazamacrocyclic and BINAM Moieties: Synthesis and Evaluation as Fluorescent Detectors

“…[6,7] Macrocyclic derivatives of BINOL were also obtained employing imidazoline linkers, [8] but in many cases BINOL was rather attached as an exocyclic structural fragment to other macrocycles such as triazacyclononane (sensor of tartrate anion), [9] calix [4]crown ether, [10] crown ethers containing additional exocyclic chiral groups. [11] Additional chromophore [12] and fluorophore [13] groups were introduced in BINOL-crown ether conjugates to ensure better optical response. Even a cryptand possessing two BINOL and two coplanar porphyrins was contrived for better coordination.…”

Enantioselective Friedel–Crafts Alkylation of N‐Methylindoles with Nitroalkenes Catalyzed by Chiral Bifunctional Abietic‐Acid‐Derived Thiourea‐ZnII Complexes

“…In our previous works, we have reported that abietic acid derivatives have been used in the separations of D / L amino acids by capillary electrophoresis 8. Furthermore, our current study has shown that crown ethers based on abietic acid are highly efficient in chiral recognition 9. Encouraged by the successful use of abietic acid derivatives, we speculated that the strategy of modifying its functional groups might be additionally exploited to design a new class of chiral thiourea catalysts for Friedel–Crafts reactions.…”

Chiral BINAM-Containing Macrocycles with Endocyclic 1,8- and 1,5-Disubstituted Anthraquinone Structural Fragments

“…for tartrate ions detection bis(triazacyclononanyl) derivative of BINOL was used, [10] this moiety was introduced in the side chain of calix [4] crown ether [11] and in a chiral crown ether which was used for recognition of chiral amines and amino acids. [12] BINOLderived crown ethers containing additional dinitrophenyl chromophore [13] or exocyclic anthracene fluorophore [14] were reported. The latter compound can be used both for detecting Hg(II), Cu(II) и Zn(II) and chiral alkylammonium salts.…”