Tetrahedron

Stereoselectivity in reactions of atropisomeric lactams and imides

…, PA Cooke, CRA Godfrey, PL Pickering, NS Simpkins…

Index: Bennett, D. Jonathan; Blake, Alexander J.; Cooke, Paul A.; Godfrey, Christopher R.A.; Pickering, Paula L.; Simpkins, Nigel S.; Walker, Matthew D.; Wilson, Claire Tetrahedron, 2004 , vol. 60, # 20 p. 4491 - 4511

Full Text: HTML

Citation Number: 30

Abstract

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. ...