Photochemical synthesis and properties of axially chiral naphthylpyridines
Five alkynyl pyridines were prepared and cyclized to naphthylpyridines as the main products in the course of a Photo-Dehydro-Diels-Alder reaction. Four of the final products are axially chiral and the determination of the rotational barrier by DFT calculations, dynamic NMR and HPLC experiments is demonstrated.
► Naphthylpyridines are accessible by Photo-Dehydro-Diels-Alder reaction. ► Most of these Naphthylpyridines are axially chiral. ► Determination of the rotational barrier of the atropisomerization can be determined by. ► dynamic NMR or HPLC and calculated using DFT methods.
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 222, Issue 1, 5 July 2011, Pages 263–265