%0 Journal Article %A Adam, Waldemar %A Bottke, Nils %A Krebs, Oliver %D 2000 %T Steric and Conformational Control of the Regioselectivities in the Ene Reaction with Trisubstituted Cycloalkenes:  Comparison of the Enophiles Singlet Oxygen, Triazolinedione, and Nitrosoarene %U https://acs.figshare.com/articles/journal_contribution/Steric_and_Conformational_Control_of_the_Regioselectivities_in_the_Ene_Reaction_with_Trisubstituted_Cycloalkenes_Comparison_of_the_Enophiles_Singlet_Oxygen_Triazolinedione_and_Nitrosoarene/3737205 %R 10.1021/ol006475c.s001 %2 https://acs.figshare.com/ndownloader/files/5828973 %K Enophiles Singlet Oxygen %K twix regioselectivity %K Ene Reaction %K nitrosoarene ene reaction %K hydroxylamine ene products 1 %K enophile attack %K Conformational Control %K abstraction %K transannular interactions %K Steric interactions %K 4 twix %K 4 proceeds %K factors dictates %K nitrosoarene enophile %X The nitrosoarene ene reaction with the cycloalkenes 13 and E-4 proceeds in high twix regioselectivity to afford the hydroxylamine ene products 1a4a (twix) and 1b4b (twin, except far E-4 twix). Steric interactions in the enophile attack are responsible for the skew trajectory of the nitrosoarene enophile. For Z-1-methylcyclooctene (Z-4), twin abstraction dominates, caused by conformational constraints (transannular interactions) in the hydrgogen-atom abstraction. The balance between these steric and conformational factors dictates the regioselectivity in the ene reaction %I ACS Publications