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

Jonathan Clayden; Christel J. Menet

doi:10.1016/S0040-4039(03)00545-8

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

Jonathan Clayden^*, Christel J. Menet

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

46 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 language	English
Pages (from-to)	3059-3062
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	15
Early online date	21 Mar 2003
DOIs	https://doi.org/10.1016/S0040-4039(03)00545-8
Publication status	Published - 7 Apr 2003

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Organic & Biological

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

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.",

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T1 - 2,3-Dihydroisoindolones by cyclisation and rearomatisation of lithiated benzamides

AU - Clayden, Jonathan

AU - Menet, Christel J.

PY - 2003/4/7

Y1 - 2003/4/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0037424819

U2 - 10.1016/S0040-4039(03)00545-8

DO - 10.1016/S0040-4039(03)00545-8

M3 - Article (Academic Journal)

AN - SCOPUS:0037424819

SN - 0040-4039

VL - 44

SP - 3059

EP - 3062

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

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

Abstract

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