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

被引:10
作者
Butkus, E
Berg, U
Stoncius, A
Rimkus, A
机构
[1] Vilnius State Univ, Dept Organ Chem, LT-2006 Vilnius, Lithuania
[2] Univ Lund, Dept Chem, S-22100 Lund, Sweden
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1998年 / 11期
关键词
D O I
10.1039/a802522c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 solved 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 far by the interaction of the carbonyl and aromatic chromophores.
引用
收藏
页码:2547 / 2551
页数:5
相关论文
共 34 条