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-Halogenation and -Alkoxylation of Phenylglycine Derivatives by Pd-Mediated C-H Functionalization: Scope and Limitations.
Molecules
January 2025
Instituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC-Universidad de Zaragoza), Pedro Cerbuna 12, 50009 Zaragoza, Spain.
Orthopalladated derivatives from substituted phenylglycines [Pd(μ-Cl)(CHRC(R)(R)N(R)] () react with halogenating reagents (PhICl, Br, I) () to give the corresponding o-halogenated amino acids CH(X)RC(R)(R)N(R) (). The reaction is general and tolerates a variety of functional groups (R to R) at the aryl ring, the Cα, and the N atom. On the other hand, the reaction of [Pd(μ-Cl)(CHRC(R)(R)N(R)] () with PhI(OAc) in the presence of a variety of alcohols ROH () gives the o-alkoxylated phenylglycines CH(OR)RC(R)(R)N(R) (), also as a general process.
View Article and Find Full Text PDFDevelopment of a Combined 2D-MGD TLC/HPTLC Method for the Separation of Terpinen-4-ol and α-Terpineol from Tea Tree, , Essential Oil.
Biomolecules
January 2025
United States Department of Agriculture-Agricultural Research Service (USDA-ARS), Subtropical Horticulture Research Station (SHRS), Miami, FL 33158, USA.
Tea tree oil (TTO), acquired from (Maiden & Betche) Cheel, Myrtaceae, is a widely utilized essential oil (EO) due to its bioactive properties. The identification and quantification of TTO ingredients is generally performed by GC-MS, which provides the most accurate results. However, in some instances, the cost and time of analysis may pose a challenge.
View Article and Find Full Text PDFConformational versatility among crystalline solids of L-phenylalanine derivatives.
Acta Crystallogr C Struct Chem
February 2025
Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Intendente Güiraldes 2160, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
In this study, we present a new N-derivative of L-phenylalanine with 2-naphthaldehyde (PN), obtained by the Schiff base formation procedure and its subsequent reduction. This compound was crystallized as a zwitterion {2-[(naphthalen-2-ylmethyl)azaniumyl]-3-phenylpropanoate, CHNO}, as an anion in a sodium salt (catena-poly[[diaquasodium(I)-di-μ-aqua] 2-[(naphthalen-2-ylmethyl)amino]-3-phenylpropanoate monohydrate], {[Na(HO)](CHNO)·HO}), as a cation in a chloride salt [(1-carboxy-2-phenylethyl)(naphthalen-2-ylmethyl)azanium chloride acetic acid monosolvate, CHNO·Cl·CHCOOH], and additionally acting as a ligand in the pentacoordinated zinc compound aquabis{2-[(naphthalen-2-ylmethyl)amino]-3-phenylpropanoato-κO}zinc(II), [Zn(CHNO)(HO)] or [Zn(PN)(HO)], denoted (PN-Zn), with the amino acid derivative in its carboxylate form.
View Article and Find Full Text PDFEnantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas.
Chirality
February 2025
Department of Chemistry, Bogazici University, Istanbul, Turkey.
2-Thiohydantoin derivatives, including different substitutions at N-1 and C-5 (5-methyl-, 5-isopropyl-, 1-acetyl-5-methyl-, and 1-acetyl-5-isopropyl-) (1-4, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2-thiohydantions were obtained in the absence of any solvent via the reaction of L-amino acids with thiourea (1&2) and via the reaction of L-amino acids with NHSCN and acetic anhydride (3&4). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2-thiohydantoins were obtained although the same synthetic methods were used.
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J Am Chem Soc
January 2025
Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Precisely controlling quantum states is relevant in next-generation quantum computing, encryption, and sensing. Chiral organic chromophores host unique light-matter interactions, which allow them to manipulate the quantized circular polarization of photons. Axially chiral organic scaffolds, such as helicenes or twisted acenes, are powerful motifs in chiral light manipulation.
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