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NMR and X-ray diffraction analysis of 3-thioamido-5-phosphono-1-cyclohexene derivatives: Conformational and stereochemical assignments |
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| Authors: | Jean-Christophe Monbaliu Bernard Tinant Jacqueline Marchand-Brynaert |
| Institution: | aUnité de Chimie Organique et Médicinale, Département de Chimie, Université catholique de Louvain, Bâtiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium bUnité de Chimie Structurale et des Mécanismes Réactionnels, Département de Chimie, Université catholique de Louvain, Bâtiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium |
| Abstract: | Reaction of N-(dienyl)-4-(R)-phenyloxazolidin-2-thione (1) with 1-diethoxyphosphoryl-1-buten-3-one (2a), methyl 3-(diethoxyphosphoryl)acrylate (2b) and 3-(diethoxyphosphoryl)acrylonitrile (2c) furnished the 4 + 2] cycloadducts 3a, 3b and 3c, respectively, as single stereoisomers, confirming the efficiency of the oxazolidin-2-thione chiral auxiliary in the facial discrimination of Diels–Alder reactions. The absolute configuration of the 3,4,5-trisubstituted cyclohexene derivatives (3a–c) was established by X-ray diffraction analysis. NMR studies confirmed the relative stereochemistries and showed two possible conformers in solution. |
| Keywords: | [4 + 2] Cycloaddition Chiral 1-aminodiene Vinyl phosphonate dienophiles Asymmetric synthesis Cyclohexene conformations NMR analysis X-ray diffraction |
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