Conformational study of a-arylethylamides of (-)-camphanic acid (CROSBI ID 81152)
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Hameršak, Zdenko ; Selestrin, Ana ; Lesac, Andreja ; Šunjić, Vitomir
engleski
Conformational study of a-arylethylamides of (-)-camphanic acid
The absolute conformation and configuration of diastereomeric amides (4A, B-6A, B) of 1S, 3R)-camphanic acid (lactone of 1-hydroxy-2, 2, 3-trimethylcyclopentan-1, 3-dicarboxylic acid, (-)-camphanic acid 9 with a-arylethylamines 1-3 are deduced from H NMR data and MM2 calculations. The absolute configuration (1'S) is assigned to the 4A-6A diastereomers, and the (1'R)-configuration to the 4B-6B diastereomers ; this assignment is confirmed by the preparation of 4A and 5A from enantiomerically pure (1'S)-a-arylethylamines 1 and 2, respectively. These results also enabled the assignment of pro-R and pro-S protons in the benzyl derivative 7.
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