A new redox-sensitive protecting group for boronic acids

ORGN 460

Jun Yan, Shan Jin, sjin1@student.gsu.edu, and Binghe Wang, wang@gsu.edu. Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30303
Boronic acids have a wide variety of applications in both organic synthesis and medicinal chemistry. In the preparation of boronic acids or reactions involving boronic acids, often the protected form is used for easy purification and to avoid side reactions. In this regard, the pinacol or neopentylglycol boronate esters are commonly used. However, sometimes such esters, especially the pinacol boronate esters, are rather difficult to deprotect. Herein we report a new protecting group, 1-(4-methoxy-phenyl)-2-methyl-propane-1,2-diol that forms a stable ester with the boronic acid moiety, and can be deprotected readily under mild oxidative conditions using reagents such as DDQ.