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Determination of the Relative Configuration of a Five-Membered Lactone from Residual Dipolar Couplings


  • C.M.T. thanks Prof. Dr. M. Reggelin for his support, Dr. L. Hennig for helpful discussions, Dr. B. Luy and Prof. Dr. H. Kessler for a gift of PS sticks, and Dr. F. Delaglio for providing the program NMRPIPE and for helping us use it. C.M.T. acknowledges the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft (TH1115/1-1) for grants. R.B. acknowledges financial support by the Volkswagen Foundation as well as computer time provided by the Norddeutscher Verbund für Hoch- und Höchstleistungsrechnen (HLRN) and the Center for Scientific Computing (CSC).


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syn- oranti-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 3J coupling data equally well. Homo- and heteronuclear residual dipolar couplings were measured which indicate that 1 is trans configured.

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