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Resolution of 1-substituted-3-methyl-3-phospholene 1-oxides by molecular complex formation with TADDOL derivatives |
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| Authors: | Tibor Novk Viktria Ujj Jzsef Schindler Mtys Czugler Mikls Kubinyi Zsuzsa A Mayer Elemr Fogassy Gyrgy Keglevich |
| Institution: | aResearch Group of the Hungarian Academy of Sciences at the Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary bDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary cInstitute of Structural Chemistry, Chemical Research Center, Hungarian Academy of Sciences, 1525 Budapest, Hungary dDepartment of Physical Chemistry and Material Science, Budapest University of Technology and Economics, H-1521 Budapest, Hungary |
| Abstract: | The antipodes of 1-aryl-, 1-alkyl- and 1-alkoxy-3-methyl-3-phospholene 1-oxides 1a–h and 1-phenyl-3-methyl-3-phospholene 1-sulfide 1i were separated in good yields and high enantiomeric excesses (up to >99% ee) by resolution via formation of diastereomeric complexes with either (?)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane 2 (TADDOL) or (?)-(2R,3R)- ,,′,′-tetraphenyl-1,4-dioxaspiro4.5]decan-2,3-dimethanol 3. The stereostructure of the supramolecular formations and the absolute configurations of the 3-phospholene oxides 1a, 1e and 1f were elucidated by single crystal X-ray crystallography. CD spectroscopy was also useful in determining the absolute configurations of some phospholene oxides 1b, 1c, 1g and 1h. |
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