Premium
Resolution of 1‐ n ‐Butyl‐3‐Methyl‐3‐Phospholene 1‐Oxide With TADDOL Derivatives and Calcium Salts of O , O '‐Dibenzoyl‐(2 R ,3 R )‐ or O , O '‐di‐ p ‐Toluoyl‐(2 R ,3 R )‐tartaric Acid
Author(s) -
Bagi Péter,
Fekete András,
Kállay Mihály,
Hessz Dóra,
Kubinyi Miklós,
Holczbauer Tamás,
Czugler Mátyás,
Fogassy Elemér,
Keglevich György
Publication year - 2014
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22293
Subject(s) - chemistry , diastereomer , enantiomer , tartaric acid , chirality (physics) , absolute configuration , resolution (logic) , oxide , medicinal chemistry , stereochemistry , organic chemistry , chiral symmetry , physics , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , citric acid , quark
The resolution methods applying (−)‐(4 R ,5 R )‐4,5‐bis(diphenylhydroxymethyl)‐2,2‐dimethyldioxolane (“TADDOL”), (−)‐(2 R ,3 R )‐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‐(2 R ,3 R )‐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. Chirality 26:174–182, 2014 . © 2014 Wiley Periodicals, Inc.