In situ Synthesis of Rosin Derived Chiral Derivatizing Agents for 31p NMR Assays of Amine and Alcohol Enantiomers  

作　　者：WU Qiang YAO Gui-yang ZHANG Ye WANG Heng-shan YANG Lin ZHU Yong-tao PAN Ying-ming 

机构地区：[1]Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources,School of Chemistry & Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, P R. China

出　　处：《Chemical Research in Chinese Universities》2013年第5期894-899,共6页高等学校化学研究（英文版）

基　　金：Supported by the National Basic Research Program of China（No.2011CB512005）, the National Natural Science Foundation of China（Nos.81260472 and 21101035）, Guangxi Natural Science Foundation of China（Nos.2011GXNSFD018010 and 2010GXNSFF013001）, the Project of Ten, Hundred, Thousand Distinguished Talents in New Century of Guangxi, China （No.2007228） and the State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China （No.CMEMR2012-A14）.

摘　　要：Chiral alcohols（3, 5） 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 alcohol has been established with them used as chiral auxiliary for chiral phosphorus derivatizing agents（CPDAs） in 3Jp NMR tests. Chemical shift difference（△δp） values ranging from 4.5 to 0.15 between two dias- tereoisomers of the CPDAs and the aryl substrates were obtained. Positive △δR-S was observed for all the tested alco- hol P（III） and P（V） derivatives, while negative △δR-S was observed for all the amines.Chiral alcohols（3, 5） 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 alcohol has been established with them used as chiral auxiliary for chiral phosphorus derivatizing agents（CPDAs） in 3Jp NMR tests. Chemical shift difference（△δp） values ranging from 4.5 to 0.15 between two dias- tereoisomers of the CPDAs and the aryl substrates were obtained. Positive △δR-S was observed for all the tested alco- hol P（III） and P（V） derivatives, while negative △δR-S was observed for all the amines.

关 键 词：Chiral phosphorus derivatizing agent ROSIN ENANTIODISCRIMINATION 31p NMR 

分 类 号：O625.12[理学—有机化学] TB333[理学—化学]