Chromatographic enantiomer separation and absolute configuration of spiro[benzo-1,3-dioxole-2,9′-bicyclo[3.3.1]nonan]-2′-one and the corresponding diastereomeric hydroxy acetals

Autor:	Eugenius Butkus, Audrius Rimkus, Ulf Berg, Arvydas Stoncius
Rok vydání:	1998
Předmět:	Microcrystalline Bicyclic molecule Stereochemistry Chemistry Absolute configuration Diastereomer Chromophore Enantiomer High-performance liquid chromatography Cotton effect
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :2547-2552
ISSN:	1364-5471 0300-9580
DOI:	10.1039/a802522c
Popis:	The enantiomers of spiro[benzo-1,3-dioxole-2,9′-bicyclo[3.3.1]nonan]-2′-one 2 and the corresponding diastereomeric exo-2′- and endo-2′-hydroxy acetals 3a,b obtained from this monoacetal were resolved by HPLC on a swollen microcrystalline triacetylcellulose column. The absolute configuration of the enantiomers of 2 and 3a,b was assigned based on the signs of the Cotton effect and employing the octant rules for the carbonyl and the aromatic chromophores. The low intensity of the band at 290 nm in the CD spectrum of monoacetal 2 was accounted for by the interaction of the carbonyl and aromatic chromophores.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b6e85992bd735732bf5c60be2a66a01a https://doi.org/10.1039/a802522c Zobrazit plný text záznamu