Application of excited state meta-effect in photolabile protecting group design

ORGN 496

Pengfei Wang, wangp@uab.edu, Huayou Hu, njuhhy@hotmail.com, and Yun Wang, candybbx@yahoo.com. department of chemistry, university of alabama at birmingham, 901 14th street south, birmingham, AL 35294
In spite of advances in photolabile protecting group (PPG) development, practically useful PPGs for some important functional groups are still rare. Herein we report our effort in developing a novel class of PPGs based on the excited state meta-effect. These PPGs are readily available via simple synthetic routes from inexpensive commercial materials. Installation of protecting group to the substrates can be achieved in excellent yields. The substrates in their protected form are remarkably stable under various conditions and can be released photochemically in high efficiency. Furthermore, there is no sensitive functional group carried by the PPGs or introduced during the protecting step, which will facilitate their synthetic applications.