Determination of the stereochemistry of gamma-butyrolactones by DPFGSE-NOE experiments.
The stereochemistry of gamma-butyrolactons tetrahydro-6a-phenylfuro[3,4-b]furan-2(3H)-one (1), 1,4,5,9b-tetrahydro-3a-methylnaphtho[2,1-b]furan-2(3aH)-one (2), 1,4,5,9 b-tetrahydro-3a-methylfuro[2,3-c]quinolin-2(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 (1)H and (13)C spectra showed a single diastereomer of all the compounds. Routine 2D experiments (DQF)-COSY, HMQC/HSQC, and HMBC were used to assign (1)H and (13)C spectra completely. Diastereotopic methylene protons with resolved (1)H 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.
Xie
X
X
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, D-35032 Marburg, Germany. xie@staff.uni-marburg.de
Tschan
S
S
Glorius
F
F
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011522:Protons; D013237:Stereoisomerism
D011522:Protons; D015107:4-Butyrolactone