Mechanism, kinetics and selectivity of selenocyclization of 5-alkenylhydantoins: an experimental and computational study

• Biljana M. Šmit,
• Radoslav Z. Pavlović,
• Dejan A. Milenković and
• Zoran S. Marković

Beilstein J. Org. Chem. 2015, 11, 1865–1875, doi:10.3762/bjoc.11.200

• and are consistent with our experimental results. The preferred pathway for formation of 5-exo products is confirmed. Keywords: density functional theory; fused bicyclic hydantoins; intermediate; reaction mechanism; regioselectivity; selenocyclization; Introduction Hydantoins, a class of

• synthesis of fused bicyclic hydantoins. 1H NMR spectroscopy monitoring, as well as 1H NMR chemical shifts prediction [29][30][31][32][33][34] is used as a useful tool in the search of the most probable intermediates in the reaction. The theoretical results are discussed and compared with our experimental

• observations. Results and Discussion We have recently reported a three-step reaction sequence to cis-fused bicyclic hydantoins involving selenium-induced cyclization of 5-alkenylhydantoins as the key step [24]. The reaction is chemo- and regiospecific giving only the five-membered bicyclic hydantoins, 5-exo