210426-64-5Relevant academic research and scientific papers
A convenient synthesis of hindered N-ARYL substituted cyclic amines
Akula, Murthy R.,Kabalka, George W.
, p. 2063 - 2070 (1998)
An efficient and high yielding synthesis of N-substituted pyrrolidines and piperidines is described.
Sterically controlled, palladium-catalyzed intermolecular amination of arenes
Shrestha, Ruja,Mukherjee, Paramita,Tan, Yichen,Litman, Zachary C.,Hartwig, John F.
supporting information, p. 8480 - 8483 (2013/07/19)
We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc) 2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.
Stereoselectivity in reactions of atropisomeric lactams and imides
Bennett, D. Jonathan,Blake, Alexander J.,Cooke, Paul A.,Godfrey, Christopher R.A.,Pickering, Paula L.,Simpkins, Nigel S.,Walker, Matthew D.,Wilson, Claire
, p. 4491 - 4511 (2007/10/03)
A range of reactions of cyclic lactam systems is described in which an atropisomeric C-N axis controls the stereochemical outcome of ring substitution or addition. In the case of enantiopure menthol adducts, substitution via N-acyliminium intermediates occurred with essentially complete control. However, the range of nucleophiles that participate in the reaction is very limited and at present the removal of the N-aryl substituent is problematic. A six-membered enamide is of moderate configurational stability and the axis exerts synthetically useful levels of control over enolate alkylations of the system. A novel Lewis acid mediated enamide arylation process was identified.
