Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (10): 1663-1675.     Next Articles



魏荣宝*; 张大为; 梁 娅 ; 卢俊瑞; 李红姬   

  1. (天津理工大学化学化工学院 天津 300191)
  • 收稿日期:2007-12-09 修回日期:2008-01-25 发布日期:2008-10-20
  • 通讯作者: 魏荣宝

Anomeric Effect in Organic Chemistry

WEI, Rong-Bao*; ZHANG, Da-Wei ; LIANG, Ya; LU, Jun-Rui; LI, Hong-Ji   

  1. (College of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300191)
  • Received:2007-12-09 Revised:2008-01-25 Published:2008-10-20
  • Contact: WEI, Rong-Bao

The anomalous axial preference of electronegative substituents at the anomeric center C(1) of the pyranose ring was first noted by Edward in 1955 and was clearly defined as the anomeric effect by Lemieux and Chü, which plays a defining role in molecular conformation and reactivity, and is now recognized as one of the most important stereo-electronic effect in organic chemistry. The anomeric effect is recognized in an Lp-X-A-Y moiety as a preference for an antiperiplanar arrangement of the lone pair (Lp) and the A—Y bond, where X is a heteroatom, A is an element with intermediate electronegativity, and Y is a group with higher electronegativity (such as oxygen, nitrogen, fluorine, etc.). In this paper, the anomeric effect, general-ized anomeric effect, reverse anomeric effect, endo-anomeric effect and exo-anomeric effect are described. The potential application of the anomeric effect is supplied.

Key words: generalized anomeric effect, anomeric effect, reverse anomeric effect, hydrogen bond