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Stereochemistry and conformation of amido-phosphonocyclohexene derivatives, assigned by NMR and X-ray diffraction analyses

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Tinant, Bernard [UCL] Defacqz, Nathalie [UCL] Robiette, Raphaël [UCL] Touillaux, Roland [UCL] Marchand-Brynaert, Jacqueline [UCL]

Stereochemistry (absolute or relative) of four compounds have been established by x-ray diffraction analysis, namely: 3(R)-[4'(R)-(phenyl)oxazolidin-2-one-1-yl]-4(S)-dimethoxyphosphoryl-4-methoxycarbonyl- 1-cyclohexene (7), 3(R)-[4'-(R)-(phenyl)-oxazolidin-2-thione-1-yl]-4(S)dimethoxyphosphoryl-4-methoxycarbonyl-1-cyclohexene (8), methyl 1-dimethoxyphosphoryl-2-succinimido-3,4-epoxy-cyclohexane-l-carboxy- late (9), and 3-succinimido-4-methylcarbonyl-5-dimethoxyphosphoryl-1-cyclohexene (10). The ring conformations deduced from NMR analysis were thus fully confirmed.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2004
Language Anglais
Journal information "Phosphorus, Sulfur and Silicon and the Related Elements" - Vol. 179, no. 2, p. 389-402 (2004)
Peer reviewed yes
Publisher Taylor & Francis Ltd (Abingdon)
issn 1042-6507
e-issn 1563-5325
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Keywords amido-phosphonic derivative ; asymmetric synthesis ; conformational analysis ; Diels-Alder reaction ; NMR analysis ; x-ray structure
Links
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Bibliographic reference Tinant, Bernard ; Defacqz, Nathalie ; Robiette, Raphaël ; Touillaux, Roland ; Marchand-Brynaert, Jacqueline. Stereochemistry and conformation of amido-phosphonocyclohexene derivatives, assigned by NMR and X-ray diffraction analyses. In: Phosphorus, Sulfur and Silicon and the Related Elements, Vol. 179, no. 2, p. 389-402 (2004)
Permanent URL http://hdl.handle.net/2078.1/40347