85806-00-4Relevant academic research and scientific papers
Conformational study of α-arylethylamides of (-)-camphanic acid
Hamersak, Zdenko,Selestrin, Ana,Lesac, Andreja,Sunjic, Vitomir
, p. 1891 - 1897 (2007/10/03)
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 α- arylethylamines 1-3 are deduced from 1H NMR data and MM2 calculations. The α-arylethyl group in diastereomers A and B adopt nearly opposite absolute conformations, stabilized by hydrogen bonding in the syn-oriented O-C(1)- C(6)-N-H unit, and repulsive interaction between the 1'C-Me group and the amide C=O group. 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)-α-arylethylamines 1 and 2, respectively. These results also enabled the assignment of pro-R (H(R)) and pro-S (H(S)) protons in the benzyl derivative 7.
1H and 2H Nuclear Magnetic Resonance Determination of the Enantiomeric Purity and Absolute Configuration of α-Deuteriated Primary Carboxylic Acids, Alcohols, and Amines
Parker, David
, p. 83 - 88 (2007/10/02)
The enentiomeric composition and absolute configuration of α-deuteriated primary carboxylic acids may be accurately determined by 1H and 2H nuclear magnetic resonance analysis of the corresponding esters of (S)-methyl 2-hydroxy-2-phenylethanoate (2).Simil
