Photochemical radical cyclization reactions with imines, hydrazones, oximes and related compounds

Hydrolytic stability of hydrazones and oximes.

Molecules containing carbon–nitrogen double bonds are prevalent in both chemical and biological contexts. The foundations for our current understanding of carbon–nitrogen double-bond formation and hydrolysis were laid by seminal work on hydrazone hydrolysis and formation, and by contributions from mechanistic studies on enzymes that utilize pyridoxal phosphate. In particular, the meticulous kin...

Lewis acid-mediated radical cyclization: stereocontrol in cascade radical addition-cyclization-trapping reactions.

An efficient approach for achieving radical cyclizations by using hydroxamate ester as a coordination tether with Lewis acid was studied. The chiral Lewis acid-mediated cascade radical addition-cyclization-trapping reaction proceeded smoothly with good enantio- and diastereoselectivities, providing various chiral γ-lactams.

Construction of Five-Membered Heterocyclic Compounds via Radical Cyclization

Chemistry of Iminium Salts, Imines, and Related Compounds

Cyclization vs. cyclization/dimerization in o-amidostilbene radical cation cascade reactions: the amide question.

The n-butyramido, isobutyramido, benzamido, and furancarboxamido functions profoundly modulate the electronics of the stilbene olefinic and NH groups and the corresponding radical cations in ways that influence the efficiency of the cyclization due presumably to conformational and stereoelectronic factors. For example, isobutyramido- stilbene undergoes FeCl(3) promoted cyclization to produce on...