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

By Steven M. Allin, Christopher J. Northfield, Michael I. Page and Alexandra M.Z. Slawin


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

Topics: Q1, QD
Publisher: Elsevier
Year: 1997
DOI identifier: 10.1016/s0040-4039(97)00686-2
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