Resolution of 1‐n‐Butyl‐3‐Methyl‐3‐Phospholene 1‐Oxide With TADDOL Derivatives and Calcium Salts of O,O'‐Dibenzoyl‐(2R,3R)‐ or O,O'‐di‐p‐Toluoyl‐(2R,3R)‐tartaric Acid |
| |
| Authors: | Péter Bagi András Fekete Mihály Kállay Dóra Hessz Miklós Kubinyi Tamás Holczbauer Mátyás Czugler Elemér Fogassy György Keglevich |
| |
| Affiliation: | 1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary;2. MTA‐BME Lendület Quantum Chemistry Research Group at the;3. Department of Physical Chemistry and Material Science, Budapest University of Technology and Economics, Budapest, Hungary;4. Institute of Molecular Pharmacology, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Budapest, Hungary;5. Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Budapest, Hungary |
| |
| Abstract: | The resolution methods applying (?)‐(4R,5R)‐4,5‐bis(diphenylhydroxymethyl)‐2,2‐dimethyldioxolane (“TADDOL”), (?)‐(2R,3R)‐α,α,α',α'‐tetraphenyl‐1,4‐dioxaspiro[4.5]decan‐2,3‐dimethanol (“spiro‐TADDOL”), as well as the acidic and neutral Ca2+ salts of (?)‐O,O'‐dibenzoyl‐ and (?)‐O,O'‐di‐p‐toluoyl‐(2R,3R)‐tartaric acid were extended for the preparation of 1‐n‐butyl‐3‐methyl‐3‐phospholene 1‐oxide in optically active form. In one case, the intermediate diastereomeric complex could be identified by single‐crystal X‐ray analysis. The absolute P‐configuration of the enantiomers of the phospholene oxide was also determined by comparing the experimentally obtained and calculated CD spectra. Chirality 26:174–182, 2014. © 2014 Wiley Periodicals, Inc. |
| |
| Keywords: | alkyl‐3‐phospholene 1‐oxide P‐chirality resolution methods optical isomers X‐ray crystallography CD spectroscopy absolute P‐configuration |
|
|
