Conformational study of α-arylethylamides of (−)-camphanic acid
作者： Zdenko Hameršak , Ana Selestrin , Andreja Lesac , Vitomir Šunjić
DOI: 10.1016/S0957-4166(98)00162-1
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摘要: Abstract The absolute conformation and configuration of diastereomeric amides ( 4A , B – 6A ) (1 S ,3 R )-camphanic acid (lactone 1-hydroxy-2,2,3-trimethylcyclopentan-1,3-dicarboxylic acid, (−)-camphanic 9 with α-arylethylamines 1 3 are deduced from H NMR data MM2 calculations. α-arylethyl group in diastereomers A adopt nearly opposite conformations, stabilized by hydrogen bonding the syn -oriented O–C(1)–C(6)–N–H unit, repulsive interaction between 1′C–Me amide CO group. (1′ is assigned to diastereomers, )-configuration 4B 6B diastereomers; this assignment confirmed preparation 5A enantiomerically pure )-α-arylethylamines 2 respectively. These results also enabled pro- (H protons benzyl derivative 7 .
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