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Determination of the Relative Configuration of a Five‐Membered Lactone from Residual Dipolar Couplings
Author(s) -
Thiele Christina M.,
Marx Andreas,
Berger Robert,
Fischer Jana,
Biel Markus,
Giannis Athanassios
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200503247
Subject(s) - residual , lactone , dipole , residual dipolar coupling , materials science , chemistry , computational chemistry , mathematics , stereochemistry , algorithm , organic chemistry
syn ‐ or anti ‐pathy? Determination of the relative configuration of the α‐methylene‐γ‐butyrolactone 1 failed by conventional NMR methods, because structures in the conformational space of both diastereoisomers exist that fulfill the restraints from NOE and 3 J coupling data equally well. Homo‐ and heteronuclear residual dipolar couplings were measured which indicate that 1 is trans configured.