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

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 (2015) 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. HETEROATOM CHEMISTRY, 26 (1). pp. 79-90. ISSN 1042-7163

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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 CD spectroscopy and related quantum chemical calculations. In one instance, the single crystal of the diasteromeric 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.

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