Bis(o-nitrophenyl)ethanediol: A practical photolabile protecting group for ketones and aldehydes.
The ketals of bis(o-nitrophenyl)ethanediol and ketones or aldehydes are smoothly deprotected in neutral conditions by irradiation with 350 nm light. The chemical stability in basic, acidic, and oxidizing media makes this form of protection orthogonal to classical protecting groups. Both racemic and enantiopure forms are readily available in two steps from inexpensive starting materials.
Blanc
Aurélien
A
Department of Organic Chemistry, University of Geneva, 30, quai Ernest-Ansermet, CH-1211 Geneva 4, Switzerland. christian.bochet@unifr.ch
Bochet
Christian G
CG