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Determination of the stereochemistry of γ-Butyrolactones by DPFGSE-NOE experiments

✍ Scribed by Dr. X. Xie; S. Tschan; F. Glorius

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
557 KB
Volume
45
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The stereochemistry of γ‐butyrolactons tetrahydro‐6__a__‐phenylfuro[3,4‐b]furan‐2(3__H__)‐one (1), 1,4,5,9__b__‐tetrahydro‐3__a__‐methylnaphtho[2,1‐b]furan‐2(3__aH__)‐one (2), 1,4,5,9 b‐tetrahydro‐3__a__‐methylfuro[2,3‐c]quinolin‐2(3__aH__)‐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. Copyright © 2007 John Wiley & Sons, Ltd.

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