摘要
研究了用手性助剂冰片与 5 羟基 2 (5H) 呋喃酮 (1)缩醛化制得液体差向异构体混合物 5[(1S) 内型冰片氧基 ] 2 (5H) 呋喃酮 (4 (R) +4(S) ) (n(4 (R) )∶n(4 (S) ) =50∶50 ) ,以该混合物为底物与硫酚 (醇 )进行不对称Michael加成 ,得到 7对非对映异构体混合物 ,其中 1对固体产物 (6d(R) +6d(S) )经分步结晶分离得 6d(S) ,d .e .大于 98% .此研究为由液体差向异构体混合物获得光学纯非对映异构体提供了一种新方法 .
The asymmetric Michael addition reactions of thiophenols with liquid epimeric mixture 5 (-) bornyloxy 2(5H) furanone 4( R)+4(S ) ( n(4(R))∶n(4(S)) =50∶50)is studied, which is prepared by reaction of the chiral anxiliary borneol with 5 hydroxy 2(5H) furanone 1. 7 diastereomeric mixtures are obtained. Among them, the solid diastereoisomers 6d( R )+6d( S ) are separated by mean of preferential crystallization, which give one optically pure compound 6d( S ) with d.e.>98 % .The method provide a new route for preparing optically pure diastereoisomer based on liquid epimers.
出处
《北京师范大学学报（自然科学版）》
CAS
CSCD
北大核心
2000年第2期230-234,共5页
Journal of Beijing Normal University(Natural Science)
基金
国家自然科学基金资助项目!(2 96 72 0 0 4)
关键词
冰片
硫酚
不对称MICHAEL加成
手性助剂
呋喃酮
borneol
thiophenols
asymmetric Michael addition
preferential crystallization
epimer
diastereoisomer
