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 H-1-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.

Resolution via diastereomeric amides of enantiopure 1,4-benzoxathian-2- and 3-carboxylic acids and determination of their configuration / V. Straniero, G. Lodigiani, L. Suigo, E. Valoti. - In: CHIRALITY. - ISSN 0899-0042. - (2022), pp. 1-12. [Epub ahead of print] [10.1002/chir.23474]

Resolution via diastereomeric amides of enantiopure 1,4-benzoxathian-2- and 3-carboxylic acids and determination of their configuration

V. Straniero
Primo
;
G. Lodigiani
Secondo
;
L. Suigo
Penultimo
;
E. Valoti
Ultimo
2022

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 H-1-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.
(S)-phenylethylamine; 1,4-benzoxathiane-2-carboxamide; 1,4-benzoxathiane-3-carboxamide; 1H NMR comparison; absolute configuration determination; chiral HPLC; diastereomeric amides;
Settore CHIM/08 - Chimica Farmaceutica
Settore CHIM/06 - Chimica Organica
20-mag-2022
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/929872
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