scholarly journals Use of Axially Chiral 2′-Methoxy-1,1′-binaphthyl-2-carboxylic Acid as Chiral Derivatizing Agent for Discrimination of Enantiomeric Alcohols and Amines by1H NMR

1989 ◽  
Vol 62 (12) ◽  
pp. 3886-3891 ◽  
Author(s):  
Sotaro Miyano ◽  
Shin-ichi Okada ◽  
Hiroki Hotta ◽  
Masayuki Takeda ◽  
Takatsugu Suzuki ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Axially Chiral ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent

Synthesis of 1-fluoroindan-1-carboxylic acid (FICA) and its properties as a chiral derivatizing agent

2006 ◽  
Vol 127 (6) ◽  
pp. 760-768 ◽  
Author(s):  
Tamiko Takahashi ◽  
Hiroaki Kameda ◽  
Tomoyo Kamei ◽  
Miyuki Ishizaki
Keyword(s):  
Carboxylic Acid ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent

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

Synthesis of 1-Fluoroindan-1-carboxylic Acid (FICA) and Its Properties as a Chiral Derivatizing Agent.

ChemInform ◽  
2006 ◽  
Vol 37 (39) ◽  
Author(s):  
Tamiko Takahashi ◽  
Hiroaki Kameda ◽  
Tomoyo Kamei ◽  
Miyuki Ishizaki
Keyword(s):  
Carboxylic Acid ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent

Application of (S)-trifluorolactic acid for chiral derivatizing agent

1999 ◽  
Vol 97 (1-2) ◽  
pp. 213-221 ◽  
Author(s):  
Toshio Kubota ◽  
Jun Kanega ◽  
Toshimasa Katagiri
Keyword(s):  
Derivatizing Agent ◽  
Chiral Derivatizing Agent

The Theoretical Basis for Assignment by NMR

2015 ◽  
Author(s):  
Josi M. Seco ◽  
Emilio Quiqoa ◽  
Ricardo Riguera
Keyword(s):  
Absolute Configuration ◽  
Chiral Auxiliary ◽  
Primary Amines ◽  
Primary Alcohols ◽  
Chiral Reagent ◽  
Chiral Compounds ◽  
Configurational Assignment ◽  
Derivatizing Agent ◽  
Chiral Derivatizing Agent ◽  
Diastereomeric Complexes

The nuclear magnetic resonance (NMR) spectra of two enantiomers are identical. Thus, the first step in using NMR to distinguish between two enantiomers should be to produce different spectra that eventually can be associated with their different stereochemistry (i.e., the assignment of their absolute configuration). Therefore, it is necessary to introduce a chiral reagent in the NMR media. There are two ways to address this problem. One is to use a chiral solvent, or a chiral agent, that combines with each enantiomer of the substrate to produce diastereomeric complexes/associations that lead to different spectra. This is the so-called chiral solvating agent (CSA) approach; it will not be further discussed here [33–34]. The second approach is to use a chiral auxiliary reagent [13–15] (i.e., a chiral derivatizing agent; CDA) that bonds to the substrate by a covalent linkage. Thus, in the most general method, the two enantiomers of the auxiliary CDA react separately with the substrate, giving two diastereomeric derivatives whose spectral differences carry information that can be associated with their stereochemistry. The CDA method that employs arylalcoxyacetic acids as auxiliaries is the most frequently used. It can be applied to a number of monofunctionals [14–15] (secondary alcohols [35–43], primary alcohols [44–46], aldehyde [47] and ketone cyanohydrins [48–49], thiols [50–51], primary amines [52–56], and carboxylic acids [57–58]), difunctional [13] (sec/sec-1,2-diols [59–61], sec/sec-1,2-amino alcohols [62], prim/sec-1,2-diols [63–65], prim/sec-1,2-aminoalcohols, and sec/prim-1,2-aminoalcohols [66–68]), and trifunctional (prim/sec/sec-1,2,3-triols [13, 69–70]) chiral compounds. Its scope and limitations are well established, and its theoretical foundations are well known, making it a reliable tool for configurational assignment. Figure 1.1 shows a summary of the steps to be followed for the assignment of absolute configuration of a chiral compound with just one asymmetric carbon and with substituents that, for simplicity, are assumed to resonate as singlets. Step 1 (Figure 1.1a): A substrate of unknown configuration (?) is separately derivatized with the two enantiomers of a chiral auxiliary reagent, (R)-Aux and (S)-Aux, producing two diastereomeric derivatives.

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