Highly Enantioselective Extraction of Phenylglycine by a Chiral Macrocyclic Receptor Based on Supramolecular Interactions

Turiel, María G.; Garrido‐González, José J.; Simón, Luis; Sanz, Francisca; Lithgow, Anna M.; Morán, Joaquı́n R.; Arriba, Ángel L. Fuentes de; Alcázar, Victoria

doi:10.1021/acs.orglett.9b04379

Cited by 14 publications

(7 citation statements)

References 35 publications

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“…The macrocycle (S)-51 was synthesized from (S)-49 (R = n C 4 H 9 ) and used for enantioselective extraction of phenylglycine from aqueous solution to chloroform. 135 When (S)-or (R)-3,3′-diformylBINOL was treated with concentrated sulfuric acid at 40 °C for 18 h followed by addition of Na 2 CO 3 , compound (S)-or (R)-52 was obtained in 24% yield (Scheme 13). 136 (S)-or (R)-52 was used as a water-soluble fluorescent probe for the enantioselective recognition of amino acids in aqueous solution.…”

Section: Sulfonation or Thiolationmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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1,1′-Bi-2-naphthol (BINOL) has been extensively used as the chirality source in the fields of molecular recognition, asymmetric synthesis, and materials science. The direct electrophilic substitution at the aromatic rings of the optically active BINOL has been developed as one of the most convenient strategies to structurally modify BINOL for diverse applications. High regioselectivity has been achieved for the reaction of BINOL with electrophiles. Depending upon the reaction conditions and substitution patterns, various functional groups can be introduced to the specific positions, such as the 6-, 5-, 4-, and 3-positions, of BINOL. Ortho-lithiation at the 3-position directed by the functional groups at the 2-position of BINOL have been extensively used to prepare the 3- and 3,3′-substituted BINOLs. The use of transition metal-catalyzed C–H activation has also been explored to functionalize BINOL at the 3-, 4-, 5-, 6-, and 7-positions. These regioselective substitutions of BINOL have allowed the construction of tremendous amount of BINOL derivatives with fascinating structures and properties as reviewed in this article. Examples for the applications of the optically active BINOLs with varying substitutions in asymmetric catalysis, molecular recognition, chiral sensing and materials are also provided.

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Section: Sulfonation or Thiolationmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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“…7,15,[42][43][44][45] By comparison, enantioselective liquid-liquid extraction (ELLE) can offer a low solvent consumption process and overcome the utilization of CSPs at the expense of enantioselectivity. 21,[46][47][48] However, commonly used chiral selectors (CSs) suffer from high volatility, ammability and biotoxicity, and are generally specialized for resolving amino acids. 11,[16][17][18][19][20][21] Therefore, amino acid-and cyclodextrinbased chiral ionic liquids (CILs) and deep eutectic systems (DES) are emerging alternatives for more eco-friendly and generic ELLE processes.…”

Section: Introductionmentioning

confidence: 99%

Strategies for chiral separation: from racemate to enantiomer

Sui,

Wang,

Wang

et al. 2023

Chem. Sci.

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“…On the other hand, the skeleton of carbazole-1,8-disulfonamides has unique advantages as an ideal molecular platform for developing anion receptors, 16,[19][20][21][22][23] based on the following reasons: firstly, carbazole NH itself and its two adjacent sulfonamide NHs can easily work together to facilitate anion binding via three convergent N-H hydrogen bond donors. Secondly, compared with the most-commonly used amide group, its analogous sulfonamide group has a more acidic NH proton and is thus a better hydrogen bond donor.…”

Section: Introductionmentioning

confidence: 99%