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Lipophilic Tartaric Acid Esters as Enantioselective Ionophores
Author(s) -
Prelog Vladimir,
Kovačević Miće,
Egli Martin
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198911473
Subject(s) - chemistry , stereoselectivity , tartaric acid , ammonium , moiety , enantiomer , alcohol , salt (chemistry) , organic chemistry , enantioselective synthesis , catalysis , citric acid
Tartaric acid esters with lipophilic alcohol moieties can discriminate between enantiomeric ammonium ions such as norephedrinium ions. Quantitative results were obtained by partitioning the components between water and 1, 2‐dichloroethane. The stereoselectivity was characterized by the free energy difference of the partition process (ΔΔ G ). Diamond‐lattice sectors were used to construct models of the (unstable) lipophilic ester/ammonium salt complexes from X‐ray structures of the individual components (esters and ammonium salts). These models can be used to interpret the effect of structure and configuration of the alcohol moiety on the stereoselectivity and enantioselectivity towards 1‐phenyl‐2‐amino‐1‐propanol (norephedrine) salts.