title: 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.
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 Ca(2+) 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.
authors: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary.
authors: Péter
authors: P
authors: Bagi
authors: András
authors: A
authors: Fekete
authors: Mihály
authors: M
authors: Kállay
authors: Dóra
authors: D
authors: Hessz
authors: Miklós
authors: M
authors: Kubinyi
authors: Tamás
authors: T
authors: Holczbauer
authors: Mátyás
authors: M
authors: Czugler
authors: Elemér
authors: E
authors: Fogassy
authors: György
authors: G
authors: Keglevich
mesh_terms: D002118:Calcium / Q000737:chemistry*; D003498:Cyclic P-Oxides / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*; D004148:Dioxolanes / Q000737:chemistry*; D000432:Methanol / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism; D013644:Tartrates / Q000737:chemistry*
chemical_list: D003498:Cyclic P-Oxides; D004148:Dioxolanes; D009943:Organophosphorus Compounds; D012492:Salts; D013644:Tartrates; C516101:alpha,alpha,alpha',alpha'-tetraaryl-1,3-dioxolane-4,5-dimethanol; D002118:Calcium; C029768:tartaric acid; D000432:Methanol
keywords: CD spectroscopy; P-chirality; X-ray crystallography; absolute P-configuration; alkyl-3-phospholene 1-oxide; optical isomers; resolution methods