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Study on synthesis of lanthanide chelates of ( l )‐α‐trifluoromethyl‐polyfluoroalkyl‐β‐diketone and their application as chiral shift reagents
Author(s) -
Huang WeiYuan,
Zhang LongQing
Publication year - 1989
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19890070213
Subject(s) - chemistry , reagent , lanthanide , trifluoromethyl , enantiomer , chelation , solubility , solvent , enantiomeric excess , proton nmr , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , ion , alkyl
The lanthanide chelates of ( l )‐2, 2‐dimethyl‐6‐trifluoromethyl‐7‐oxa‐6, 8, 8, 9, 9, 10, 10, 10‐octafluoro‐3, 5‐decanedione, Ln [( l )‐CF 3 CF 2 CF 2 OCF (CF 3 ) COCHCOC (CH 3 ) 3 ] 3 ( l ‐3a, Ln=Eu; 3b, Ln=Pr), are useful as 1 H NMR shift reagents for direct determination of enantiomeric composition of enantiomorphous alcohols, ketones and amines. With these substrates, l ‐3a induces shift difference similar to that induced by Eu(facam) 3 and Eu(hfbc) 3 . However, due to the higher solubility of the chelates l ‐3a and l ‐3b in nonpolar organic solvent such as CHCl 3 , CCl 4 and only one 1 H signal from l ‐3a and l ‐3b is observed, their application as the new chiral shift reagents seems promising. The spectral nonequivalence is also observed for dimethylsulfoxide in the presence of l ‐3a.