Roof shape chiral alcohol: auxiliary for asymmetric synthesis of α-halo acid derivatives

Jain, Nayan; Bedekar, Ashutosh V.

doi:10.1016/j.tetlet.2016.01.003

Cited by 3 publications

(1 citation statement)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We have previously presented the synthesis and resolution of roof shape alcohols I and II and their derivatives (Chart ). , The optically pure roof-shape alcohols were also converted to amines III and IV to be scanned as chiral solvating agents for discrimination of the signals of some optically active compounds in NMR spectroscopy, while we also used I as a chiral auxiliary for asymmetric synthesis of α-halo acids…”

Section: Introductionmentioning

confidence: 99%

Application of Roof-Shape Amines as Chiral Solvating Agents for Discrimination of Optically Active Acids by NMR Spectroscopy: Study of Match–Mismatch Effect and Crystal Structure of the Diastereomeric Salts

2016

Self Cite

View full text Add to dashboard Cite

Optically active roof-shape amines were prepared and scanned as chiral solvating agents to study molecular recognition of acids by NMR analysis. Three types of amines were studied to establish a match-mismatch effect for structurally diverse acid analytes. Single-crystal X-ray diffraction analysis was performed on the diastereomeric salts of roof-shape amines and both isomers of mandelic acid to establish molecular conformation and correlate the absolute configuration with the observed NMR shift. The present system also recognizes the two isomers of weakly acidic BINOL and its derivatives.

show abstract

Section: Introductionmentioning

confidence: 99%

Application of Roof-Shape Amines as Chiral Solvating Agents for Discrimination of Optically Active Acids by NMR Spectroscopy: Study of Match–Mismatch Effect and Crystal Structure of the Diastereomeric Salts

2016

Self Cite

View full text Add to dashboard Cite

show abstract

Effect of Substituent of Roof Shape Amines on the Molecular Recognition of Optically Active Acids by NMR Spectroscopy

2020

Self Cite

View full text Add to dashboard Cite

Optically active roof shape derivatives of benzyl amines were synthesized and screened as chiral solvating agents for the study of molecular recognition of chiral compounds by NMR and UV spectroscopy. The effect of substituents on the aromatic ring of benzyl unit is investigated to assess the binding ability with the analyte and an experimental correlation is observed. Altering the substituents on the ring of benzyl amine and the acidic substrates, significantly influence the CSA interactions. The supramolecular interactions between acid and amine in the single crystal X-ray analysis of the diastereomeric salts provide further insight of the mode of molecular recognition.

show abstract

Applications of chiral naphthyloxycyclohexanols in deracemization of α-substituted carboxylic acids by dynamic thermodynamic resolution

2019

View full text Add to dashboard Cite

show abstract

Roof shape chiral alcohol: auxiliary for asymmetric synthesis of α-halo acid derivatives

Cited by 3 publications

References 63 publications

Application of Roof-Shape Amines as Chiral Solvating Agents for Discrimination of Optically Active Acids by NMR Spectroscopy: Study of Match–Mismatch Effect and Crystal Structure of the Diastereomeric Salts

Application of Roof-Shape Amines as Chiral Solvating Agents for Discrimination of Optically Active Acids by NMR Spectroscopy: Study of Match–Mismatch Effect and Crystal Structure of the Diastereomeric Salts

Effect of Substituent of Roof Shape Amines on the Molecular Recognition of Optically Active Acids by NMR Spectroscopy

Applications of chiral naphthyloxycyclohexanols in deracemization of α-substituted carboxylic acids by dynamic thermodynamic resolution

Contact Info

Product

Resources

About