F-THENA: a chiral derivatizing agent for the determination of the absolute configuration of secondary aromatic alcohols with a self-validating system

2016 ◽  
Vol 14 (46) ◽  
pp. 11002-11012 ◽  
Author(s):  
Kulvadee Dolsophon ◽  
Jakapun Soponpong ◽  
Jittra Kornsakulkarn ◽  
Chawanee Thongpanchang ◽  
Samran Prabpai ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
H Nmr ◽  
System P ◽  
Aromatic Alcohols ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent ◽  
The Absolute

F-THENA can be used with 19F- and 1H-NMR to assign the configuration of 2° aromatic alcohols with a self-validation system.

Tetrahydro-1,4-epoxynaphthalene-1-carboxylic acid: a chiral derivatizing agent for the determination of the absolute configuration of secondary alcohols

2010 ◽  
Vol 51 (38) ◽  
pp. 4965-4967 ◽  
Author(s):  
Suttipun Sungsuwan ◽  
Nopporn Ruangsupapichart ◽  
Samran Prabpai ◽  
Palangpon Kongsaeree ◽  
Tienthong Thongpanchang
Keyword(s):  
Carboxylic Acid ◽  
Absolute Configuration ◽  
Secondary Alcohols ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent ◽  
The Absolute

2-Cyano-2-indolylpropanoic acid as a chiral derivatizing agent for the absolute configuration assignment of secondary alcohols and primary amines by 1 H NMR and VCD

2017 ◽  
Vol 28 (6) ◽  
pp. 762-782 ◽  
Author(s):  
Claudia I. Bautista-Hernández ◽  
Nayely Trejo-Carbajal ◽  
Erick A. Zúñiga-Estrada ◽  
Alberto Aristeo-Dominguez ◽  
Myriam Meléndez-Rodríguez ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Primary Amines ◽  
Secondary Alcohols ◽  
H Nmr ◽  
Configuration Assignment ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent ◽  
The Absolute

Determination of the absolute configuration of the fragments composing the phytotoxin phomalide

1997 ◽  
Vol 75 (3) ◽  
pp. 314-317 ◽  
Author(s):  
M. Soledade C. Pedras
Keyword(s):  
Absolute Configuration ◽  
Capillary Column ◽  
Acid Methyl Ester ◽  
Isopropyl Ester ◽  
H Nmr ◽  
Acid Methyl ◽  
The Absolute ◽  
Amino Acid Methyl Ester ◽  
Unambiguous Assignment

The absolute configurations of the residues constituting phomalide (1) were determined on the products resulting from acidic hydrolysis. The configurations of the amino acids Val and Leu were determined as (S) and (R), respectively, by chiral GC analysis (Chirasil-Val capillary column), employing N-trifluoroacetyl (TFA) amino acid methyl ester derivatives. The configurations of the hydroxy acids O-Phe and O-Leu were determined as (S) by 1H NMR of the Mosher's esters of the isopropyl ester derivatives. The method described allowed for the unambiguous assignment of the absolute configuration of the α-amino and α-hydroxy acid residues composing phomalide (1). Keywords: absolute configuration, depsipeptide, Mosher's ester.

FICA, a new chiral derivatizing agent for determining the absolute configuration of secondary alcohols by 19F and 1H NMR spectroscopies

2013 ◽  
Vol 24 (17) ◽  
pp. 1001-1009 ◽  
Author(s):  
Tamiko Takahashi ◽  
Hiroaki Kameda ◽  
Tomoyo Kamei ◽  
Jyunichi Koyanagi ◽  
Fabio Pichierri ◽  
...  
Keyword(s):  
1H Nmr ◽  
Absolute Configuration ◽  
Secondary Alcohols ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent ◽  
The Absolute

Determination of the absolute stereochemistry of the fungal metabolite (R)-(−)-2-(4′-hydroxyphenyl)-2-hydroxyethanoic acid (pisolithin B)

1991 ◽  
Vol 69 (5) ◽  
pp. 772-778 ◽  
Author(s):  
Youla S. Tsantrizos ◽  
Kelvin K. Ogilvie
Keyword(s):  
Absolute Configuration ◽  
Lithium Aluminum Hydride ◽  
Optical Rotation ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Fungal Metabolite ◽  
H Nmr ◽  
The Absolute ◽  
Absolute Stereochemistry

The antifungal antibiotic pisolithin B (p-hydroxymandelic acid, 2-(4′-hydroxyphenyl)-2-hydroxyethanoic acid, 1a) was shown to have the absolute (R) configuration. The stereochemistry was established via comparison of its optical rotation to that of its synthetic (R) and (S) enantiomers. The synthetic samples were prepared by the stereospecific reduction of the prochiral α-keto acid, p-hydroxybenzoylformic acid (2-(4′-hydroxyphenyl)-2-oxoethanoic acid, 2a), with (R) or (S)-2,2′-dihydroxy-1,1′-binaphthyl lithium aluminum hydride (BINAL-H). The absolute configuration and enantiomeric purity of both products were determined using the 1H NMR of their isobutyl esters in the presence of the chiral solvating agent (R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol. Key words: pisolithin B, p-hydroxymandelic acid, antifungal, absolute configuration.

1H—NMR-spektroskopische Bestimmung der diastereomeren Reinheit und der absoluten Konfiguration am Phosphoratom von tButyl-phenyl-phosphinsäure-(—)-menthylester / Determination of the Diastereomeric Purity and the Absolute Configuration at Phosphorus of tButyl-phenyl-phosphinic Acid (—)-Menthyl Ester by Means of 1H NMR Spectroscopy

1977 ◽  
Vol 32 (5) ◽  
pp. 589-593 ◽  
Author(s):  
Reiner Luckenbach ◽  
Hans-H. Bechtolsheimer
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
Absolute Configuration ◽  
1H Nmr Spectroscopy ◽  
Nmr Spectra ◽  
Phosphinic Acid ◽  
H Nmr ◽  
The Absolute ◽  
Diastereomeric Purity

The preparation and separation into diastereomers of tbutyl-phenyl-phosphinic acid (—)-menthyl ester (1a) is reported. The diastereomeric purity as well as the absolute configuration at phosphorus of 1 a can be deduced from the detailed analysis of the 1H NMR spectra of samples of 1a differing in their diastereomer ratios.

ChemInform Abstract: FICA (I), a New Chiral Derivatizing Agent for Determining the Absolute Configuration of Secondary Alcohols by19F and1H NMR Spectroscopies.

ChemInform ◽  
2014 ◽  
Vol 45 (6) ◽  
pp. no-no
Author(s):  
Tamiko Takahashi ◽  
Hiroaki Kameda ◽  
Tomoyo Kamei ◽  
Jyunichi Koyanagi ◽  
Fabio Pichierri ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Secondary Alcohols ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent ◽  
The Absolute
Sign in / Sign up

Export Citation Format

Share Document