摘要
以松香为原料通过三步反应高产率合成手性二醇3和手性单醇6,将它们用作手性助剂现场制备有机膦衍生试剂,分别对单官能团手性底物(单胺、单醇)和双官能团底物(双胺、双醇及氨基醇)进行衍生,通过31P NMR测定,其芳基底物非对映体衍生物的膦化学位移差异值(Δδp)在3.08～0.10之间,均能够在测定条件下实现对映体峰的基线分离.用于α-萘乙胺和1,1'-联二萘酚(BINOL)样品对映体过量值测定,相对误差小于±2%.
Chiral alcohols 3 and 6 were synthesized in optically pure forms from easily available rosin acid in short-steps. A comprehensive protocol for the enantiomeric excess assays of mono- or di-functional-grouped chiral secondary amine or al- cohol has been established by using them as chiral auxiliary for chiral phosphorus derivatizing reagents （CPDA） in ^31p NMR tests. Chemical shift difference （△δp） values ranging from 3.08 to 0.10 between two diastereoisomers of the CPDAs and the aryl substrates were obtained. The enantiomeric excess of 1-（1-naphthyl）ethylamine and 1,1＇-bi（2-naphthol） is determined using our CPDA, and the results showed that the relative error was less than ±2%.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2012年第5期900-906,共7页
Chinese Journal of Organic Chemistry
基金
973计划前期研究专项(No.2011CB512005)
国家自然科学基金(No.20762001)
广西自然科学基金重点(No.2011GXNSFD018010)
广西新世纪十百千人才工程人选(No.2007228)资助项目~~
关键词
31PNMR
对映体过量检测
松香基膦试剂
^31p NMR
enantiomeric excess detection
rosin derived phosphine agents
