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

摘要

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 Ca2+ 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.