%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 1−3 and E-4 proceeds in high twix regioselectivity to afford the hydroxylamine ene
products 1a−4a (twix) and 1b−4b (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