A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives

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

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44 Citations (Scopus)


A highly diastereoselective method for the synthesis of 3-substituted isoindolin-1-ones has been developed through application of a tricyclic lactam substrate as an N-acyliminium ion precursor. Ring-opening of the tricyclic lactam with triethylsilane as hydride source generates the targets with up to exclusive levels of diastereoselectivity. This approach compliments that reported in the preceding paper. (C) 1998 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)143-146
Number of pages4
JournalTetrahedron Letters
Issue number1
Publication statusPublished - 1 Jan 1999


  • amino alcohols
  • aminals
  • diastereocontrol
  • transition states
  • nitrogen heterocycles


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