2,3-Dihydroisoindolones by cyclisation and rearomatisation of lithiated benzamides

Jonathan Clayden*, Christel J. Menet

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

43 Citations (Scopus)

Abstract

Lithiation of tertiary aromatic N-benzyl amides generates [α]-amido benzyllithiums which cyclise with dearomatisation to cyclic extended enolates. Rearomatisation by oxidation, or, in the case of methoxy-substituted enolates, elimination, yields 2,3-dihydroisoindoles. Enantiomerically enriched products may be formed either by using a chiral base to lithiate the starting material or by using a chiral starting material.

Original languageEnglish
Pages (from-to)3059-3062
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number15
Early online date21 Mar 2003
DOIs
Publication statusPublished - 7 Apr 2003

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