720712-01-6Relevant academic research and scientific papers
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.
