A Highly Diastereoselective Synthesis of Tricyclic Lactams and their Application as Novel N-Acyl Iminium Ion Precursors in the Synthesis of Isoindolinone Derivatives

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

Research output: Contribution to journalArticle

50 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3627-3630
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number20
DOIs
Publication statusPublished - 19 May 1997

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