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Using a Combination of Magnetic Anisotropic Effects for the Configurational Assignment of Amino Alcohols
Author(s) -
Leiro Victoria,
Seco José Manuel,
Quiñoá Emilio,
Riguera Ricardo
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000229
Subject(s) - stereocenter , chemistry , anisotropy , phenylacetic acid , absolute configuration , chemical shift , carbon fibers , hydrogen , asymmetric carbon , spectroscopy , computational chemistry , stereochemistry , organic chemistry , materials science , enantioselective synthesis , physics , catalysis , optically active , quantum mechanics , composite number , composite material
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 Δ δ 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.