Photocatalyzed Multiple Additions of Amines to α,β-Unsaturated Esters and Nitriles

Article abstract of DOI:10.1021/jo00082a021

Photoelectron-transfer-catalyzed intermolecular carbon-carbon bond formation of primary, secondary, and tertiary amines with α,β-unsaturated esters and nitriles using photosensitizers such as anthraquinone, acridone, and dicyanoanthracene has been investigated.The addition of α-aminoalkyl radicals, generated via photoelectron-transfer processes, to olefinic substrates and the subsequent 1,5-hydrogen abstraction reactions of the amine-olefin adduct radicals lead to a number of interesting multiple-olefin-added products.The adducts of the primary and secondary amines with α,β-unsaturated esters undergo further cyclizations to give spiro and cyclic lactams, respectively.