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- Title
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-(2 R,3 R)-tartaric Acids
- Authors
Bagi, Péter; Fekete, András; Kállay, Mihály; Hessz, Dóra; Kubinyi, Miklós; Holczbauer, Tamás; Czugler, Mátyás; Fogassy, Elemér; Keglevich, György
- Abstract
ABSTRACT The resolution of 1- i-butyl-3-methyl-3-phospholene 1-oxide was studied applying TADDOL [(−)-(4 R,5 R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane], spiro-TADDOL [(−)-(2 R,3 R)-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-(2 R,3 R)-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.
- Subjects
DIASTEREOISOMERS; DIASTEREOISOMERIZATION; CALCIUM salts; OXIDES; CIRCULAR dichroism; QUANTUM chemistry
- Publication
Heteroatom Chemistry, 2015, Vol 26, Issue 1, p79
- ISSN
1042-7163
- Publication type
Article
- DOI
10.1002/hc.21218