2005
DOI: 10.1590/s0100-40422005000600022
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Utilização de RMN de ¹H na determinação da configuração absoluta de álcoois

Abstract: DdR,S = deltaR - deltaS) are measured. The determination of the absolute configuration of the alcohol molecule is based on the correlation between its chiral center and the auxiliary reagent's chiral center. Therefore, the determination of the absolute configuration depends on aromatic ring shielding effects on the substituents of the alcohol as evidenced by the ¹H NMR spectrum.]]>

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Cited by 3 publications
(2 citation statements)
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“…α-Methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA, 26 ), also known as Mosher’s reagent, is used as a chiral derivatizing agent for defining both absolute configurations and enantiomeric excess of natural and synthetic amines and alcohols by NMR spectroscopy. 25 26 MTPA chloride enantiomers used as chiral derivatizing agents are commercially available, but these are expensive, moisture sensitive, and stored at a low temperature. To overcome these limitations, the Katritzky group established a protocol for the synthesis of enantiomeric and racemic form of 1-benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one (Mosher-Bt reagent) 27 in ( R )- 27 , and ( S )- 27 , rac - 27 forms by refluxing the MTPA 26 with BtH and thionyl chloride in acetonitrile/water (2:1) for 50 h. The prepared Mosher-Bt reagent 27 was reacted with various chiral amino acids 28 and peptides to obtain the corresponding amides 29 to prove the efficacy of the developed Mosher-Bt reagent over the sensitive MTPA chloride (Scheme 17 ).…”
Section: Applications Of N -Acylbenzotriazoles In Org...mentioning
confidence: 99%
“…α-Methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA, 26 ), also known as Mosher’s reagent, is used as a chiral derivatizing agent for defining both absolute configurations and enantiomeric excess of natural and synthetic amines and alcohols by NMR spectroscopy. 25 26 MTPA chloride enantiomers used as chiral derivatizing agents are commercially available, but these are expensive, moisture sensitive, and stored at a low temperature. To overcome these limitations, the Katritzky group established a protocol for the synthesis of enantiomeric and racemic form of 1-benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one (Mosher-Bt reagent) 27 in ( R )- 27 , and ( S )- 27 , rac - 27 forms by refluxing the MTPA 26 with BtH and thionyl chloride in acetonitrile/water (2:1) for 50 h. The prepared Mosher-Bt reagent 27 was reacted with various chiral amino acids 28 and peptides to obtain the corresponding amides 29 to prove the efficacy of the developed Mosher-Bt reagent over the sensitive MTPA chloride (Scheme 17 ).…”
Section: Applications Of N -Acylbenzotriazoles In Org...mentioning
confidence: 99%
“…Esta técnica simples também é amplamente empregada no estudo de compostos que apresentem um grupamento quiral em sua estrutura, tais como, peptídeos, ácidos nucleicos, taninos e carboidratos. [187][188][189] O espectro de CD registra a diferença entre a absorção de luz circularmente polarizada para a direita e para a esquerda em função do comprimento de onda, de acordo com a equação 5.…”
Section: Análise Conformacional Da Hsa Por Espectroscopia De Dicroísmunclassified