Determination of the stereochemistry of gamma-butyrolactones by DPFGSE-NOE experiments

Xie X, Tschan S, Glorius F

Forschungsartikel (Zeitschrift)

Zusammenfassung

The stereochemistry of gamma-butyrolactons tetrahydro-6a-phenylfuro[3,4-b]furan-2(3H)-one (1),1,4,5,9btetrahydro-3a-methylnaphtho[2,1-blfuran-2(3aH)-one (2),1,4,5,9 b-tetrahydro-3a-methylfuro[2,3-c]quinolin2-(3aH)-one (3) and hexahydro-furo[3,2-c]benzofuran-2-one (4) was studied using DPFGSE-NOE experiments. Compounds 1-3 contain two stereocenters, while 4 contains three. Both H-1 and C-13 spectra showed a single diastereomer of all the compounds. Routine 2D experiments (DQB)-COSY, HMQC/HSQC, and HMBC were used to assign H-1 and C-13 spectra completely. Diastereotopic methylene protons with resolved H-1 NMR signals as well as protons of cyclohexane served as references for the construction of the spatial arrangement in the molecules. NOE contacts between protons attached to the stereocenter and the diastereotopic protons were thus used to determine the configuration of the molecules. Vicinal coupling constants (3)J assisted the assignment of the conformational arrangement of the cyclohexane ring of 4. Copyright (c) 2007 John Wiley & Sons, Ltd.

Details zur Publikation

FachzeitschriftMagnetic Resonance in Chemistry
Jahrgang / Bandnr. / Volume45
Ausgabe / Heftnr. / Issue5
Seitenbereich381-388
StatusVeröffentlicht
Veröffentlichungsjahr2007 (31.05.2007)
Sprache, in der die Publikation verfasst istEnglisch
DOI10.1002/mrc.1965
StichwörterNMR stereochemistry DPFGSE-NOE gamma-butyrolactones carbene-catalyzed reaction n-heterocyclic carbenes c-13 nmr assignments conformational-analysis stereoselective-synthesis alpha; beta-unsaturated aldehydes activated carboxylates nucleophilic carbenes conjugate umpolung direct annulations

Autor*innen der Universität Münster

Glorius, Frank
Professur für Organische Chemie (Prof. Glorius)