Resolution of 1-n-propoxy-3-methyl-3-phospholene 1-oxide by diastereomeric complex formation using TADDOL derivatives and calcium salts of O,O '-dibenzoyl-(2R,3R)- or O,O '-di-p-toluoyl-(2R,3R)-tartaric acid

Bagi, Péter and Kállay, Mihály and Hessz, Dóra and Kubinyi, Miklós and Holczbauer, Tamás and Czugler, Mátyás and Keglevich, György (2014) Resolution of 1-n-propoxy-3-methyl-3-phospholene 1-oxide by diastereomeric complex formation using TADDOL derivatives and calcium salts of O,O '-dibenzoyl-(2R,3R)- or O,O '-di-p-toluoyl-(2R,3R)-tartaric acid. TETRAHEDRON-ASYMMETRY, 25 (4). pp. 318-326. ISSN 0957-4166, ESSN: 1362-511X

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Abstract

The 1-n-propoxy-3-methyl-3-phospholene 1-oxide was prepared in optically active form by extending our 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. In one case, the 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 CD spectoroscopy. Keywords: Alkoxy-3-phospholene 1-oxide; P-chirality; Resolution methods; Optical isomers; X-ray crystallography; CD-spectroscopy; Absolute P-configuration.

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