Anomeric effect
In organic chemistry, the anomeric effect or Edward-Lemieux effect (after J. T. Edward and Raymond Lemieux) is a stereoelectronic effect describing the tendency for vicinal heteroatomic substituents of a cyclic heteroatom – e.g., oxygen in a tetrahydropyran ring – to assume the relative axial orientation, rather than a less sterically-hindered equatorial orientation. This effect was first observed in pyranose rings by J. T. Edward in 1955, while studying carbohydrate chemistry.