Roof shape amines: synthesis and application as NMR chiral solvating agents for discrimination of α-functionalized acids

A series of new chiral roof shape amines have been prepared from anthracene involving simple chemical steps and enzymatic resolution of isomers. The amines were screened as chiral solvating agents for the discrimination of enantiomers of several α-functionalized acids by the 1H NMR analysis. The system can also be used to accurately measure enantiomeric excess of mandelic acid by 1H NMR analysis. The roof shape CSAs were capable of detecting the shift in the signals for the standard four nuclei of 1H, 13C, 19F and 31P of various optically active acids.

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