A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives

Allin, Steven M., Northfield, Christopher J., Page, Michael I. and Slawin, Alexandra M.Z. (1997) A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives. Tetrahedron Letters, 38 (20). pp. 3627-3630. ISSN 0040-4039

Abstract

Condensation of 2-formylbenzoic acid with α-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic γ-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives.

Item control for Repository Staff only: