Resolution of 3-methyl-3-phospholene 1-oxides by molecular complex formation with TADDOL derivatives |
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| Institution: | 1. Université Paris Saclay, CentraleSupélec, Campus de Châtenay, Grande Voie des Vignes, 92295 Châtenay-Malabry, France;2. CNRS, UMR 8580, Laboratory “Structures Propriétés et Modélisation des Solides” (SPMS), Grande Voie des Vignes, 92295 Châtenay-Malabry, France;3. Faculty of Physical Chemistry, University of Belgrade, P.O. Box 47, 11001 Belgrade, Serbia;4. Department of Physical Chemistry, Vinča Institute of Nuclear Sciences, University of Belgrade, P.O.Box 522, Belgrade, Serbia;5. University School of Medicine, Institute of Medical Chemistry, University of Belgrade, Višegradska 26, 11000 Belgrade, Serbia;6. Institute of POM-based Materials, The Synergistic Innovation Center of Catalysis Materials of Hubei Province, Hubei University of Technology, 430086 Wuhan, Hubei Province, P. R. China;7. Department of Chemistry, Tsinghua University, 100084 Beijing, P.R. China |
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| Abstract: | The antipodes of 1-phenyl-3-methyl-3-phospholene 1-oxide 1a were separated in good yield and in high enantiomeric excess (∼99% ee) by resolution via formation of diastereomeric complexes with (4R,5R)-(−)- and (4S,5S)-(+)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane 2 (TADDOL) or (−)-(2R,3R)-α,α,α′,α′-tetraphenyl-1,4-dioxaspiro4.5]decan-2,3-dimethanol 3. The method was also suitable for the resolution of the 1-ethoxy-3-phospholene derivative 1b, suggesting that our novel procedure may be of general value, both for the resolution of chiral phosphine oxides and phosphinates. |
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