Using a combination of magnetic anisotropic effects for the configurational assignment of amino alcohols.
The combined magnetic anisotropic effects generated by two auxiliary moieties of 2-methoxy-2-phenylacetic acid (MPA), introduced on two families of terminal 1,2-amino alcohols (prim/sec and sec/prim), determine the signs of the Deltadelta(RS) parameters-the differences in chemical shifts between the bis-(R)-MPA and the bis-(S)-MPA esters-of the hydrogen atoms placed at both sides of the stereogenic carbon atoms, thereby allowing the determination of the absolute configuration of those heterobifunctional compounds. Theoretical (AM1, B3LYP) and experimental (CD, (3)J, low-temperature NMR spectroscopy, isotopic labeling) studies, together with testing with a number of representative compounds, permit one to establish the foundations of this methodology.
Leiro
Victoria
V
Departamento de Química Orgánica, Facultad de Química y Unidad de RMN de Biomoléculas Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Seco
José Manuel
JM
Quiñoá
Emilio
E
Riguera
Ricardo
R
D000605:Amino Alcohols / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008280:Magnetics; D010648:Phenylacetates / Q000737:chemistry*; D013237:Stereoisomerism
D000605:Amino Alcohols; D010648:Phenylacetates; C025136:phenylacetic acid