A case study on the resolution of the 1-i-Butyl-3-methyl-3-phospholene 1-oxide via diastereomeric complex formation using TADDOL derivatives and via diastereomeric coordination complexes formed from the calcium salts of O,O′-Diaroyl-(2R,3R)-tartaric acids

Péter Bagi, András Fekete, Mihály Kállay, Dóra Hessz, Miklós Kubinyi, Tamás Holczbauer, Mátyás Czugler, Elemér Fogassy, György Keglevich

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11 Citations (Scopus)

Abstract

The resolution of 1-i-butyl-3-methyl-3-phospholene 1-oxide was studied applying TADDOL [(-)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane], spiro-TADDOL [(-)-(2R,3R)-α,α,α′,α′-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol], or the acidic and neutral Ca2+ salts of (-)-O,O′-dibenzoyl- and (-)-O,O′-di-p-toluoyl- (2R,3R)-tartaric acid as the resolving agent. The absolute configuration of the P-asymmetric center was determined by circular dichroism spectroscopy and related quantum chemical calculations. In one instance, the single crystal of the diastereomeric complex incorporating i-butyl-3-phospholene oxide and spiro-TADDOL was subjected to X-ray analysis, which suggested a feasible hypothesis for the efficiency of the resolution process under discussion that may be an example for the "solvent-inhibited" resolution.

Original languageEnglish
Pages (from-to)79-90
Number of pages12
JournalHeteroatom Chemistry
Volume26
Issue number1
DOIs
Publication statusPublished - Jan 2015

ASJC Scopus subject areas

  • Chemistry(all)

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