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NMR and X-ray diffraction analysis of 3-thioamido-5-phosphono-1-cyclohexene derivatives: Conformational and stereochemical assignments

✍ Scribed by Jean-Christophe Monbaliu; Bernard Tinant; Jacqueline Marchand-Brynaert

Publisher: Elsevier Science
Year: 2008
Tongue: English
Weight: 347 KB
Volume: 879
Category: Article
ISSN: 0022-2860
DOI: 10.1016/j.molstruc.2007.08.018

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✦ Synopsis

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.

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