Correlation between optical rotation sign and conformation of γ- butyrolactones. An empirical correlation rule to predict optical activity and stereochemistry of γ-butyrolactones

Article abstract of DOI:10.1016/S0040-4020(98)00817-5

A series of trans-4,5-disubstituted-γ-butyrolactones are found to adopt different conformations by ¹H NMR spectroscopy, whose optical rotation signs are found to depend on the conformations they assume. An empirical correlation rule is proposed for the prediction of optical activity and stereochemistry of γ-butyrolactones, which is confirmed by the X-ray analyses of (+)- and (-)-γ-butyrolactones.