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

S M Allin, C J Northfield, M I Page, A M Z Slawin

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51 Citations (Scopus)

Abstract

Condensation of 2-formylbenzoic acid with alpha-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic gamma-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. (C) 1997 Elsevier Science Ltd.

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

Keywords

  • SIMPLE ASYMMETRIC-SYNTHESIS
  • 2-SUBSTITUTED PYRROLIDINES

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