Resolution via diastereomeric amides of enantiopure 1,4-benzoxathian-2- and 3-carboxylic acids and determination of their configuration.
Chirality
; 34(8): 1053-1064, 2022 08.
Article
em En
| MEDLINE
| ID: mdl-35596548
ABSTRACT
1,4-Benzoxathiane, 2- or 3-substituted, is an important scaffold, and despite its presence in several therapeutic agents, it is chemically unexploited. Furthermore, only a few examples in literature report this moiety in its enantiopure form. Here, taking advantage to the formation of diastereomeric amides by using (S)-phenylethylamine, which show significant differences in terms of 1 H-nuclear magnetic resonance (NMR) spectra and other physical chemical properties, we defined for the first time the absolute configuration of each amide, both 2- or 3-substituted. Moreover, the diastereomeric amides were further hydrolyzed in acid conditions, letting to the achievement of the corresponding 1,4-benzoxathian carboxylic acids.
Palavras-chave
Texto completo:
1
Bases de dados:
MEDLINE
Assunto principal:
Ácidos Carboxílicos
/
Amidas
Idioma:
En
Revista:
Chirality
Assunto da revista:
BIOLOGIA MOLECULAR
/
QUIMICA
Ano de publicação:
2022
Tipo de documento:
Article
País de afiliação:
Itália