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

Bagi, Péter and Fekete, András and Kállay, Mihály and Hessz, Dóra and Kubinyi, Miklós and Holczbauer, Tamás and Czugler, Mátyás and Fogassy, Elemér and Keglevich, György (2014) 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. CHIRALITY: THE PHARMACOLOGICAL, BIOLOGICAL, AND CHEMICAL CONSEQUENCES OF MOLECULAR ASYMMETRY, 26 (3). pp. 174-182. ISSN 0899-0042

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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.

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