Anionic cyclisations of an N-benzyl naphthamide: A route to benzo[e]isoindolones

Anjum Ahmed; Jonathan Clayden; Michael Rowley

doi:10.1039/A707683E

Anionic cyclisations of an N-benzyl naphthamide: A route to benzo[e]isoindolones

Anjum Ahmed, Jonathan Clayden^*, Michael Rowley

^*Corresponding author for this work

School of Chemistry

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68 Citations (Scopus)

Abstract

On treatment with Bu^tLi and HMPA, N-tert-butyl-N-benzyl-1-naphthamide undergoes cyclisation to a tricyclic enolate which reacts diastereoselectively with electrophiles to give substituted 2,3,3a,9b-tetrahydro-1H-benzo[e]-isoindol-1-ones, the first example of an anionic cyclisation onto an aromatic ring.

Original language	English
Pages (from-to)	297-298
Number of pages	2
Journal	Chemical Communications
Issue number	3
DOIs	https://doi.org/10.1039/A707683E
Publication status	Published - 7 Feb 1998

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title = "Anionic cyclisations of an N-benzyl naphthamide: A route to benzo[e]isoindolones",

abstract = "On treatment with ButLi and HMPA, N-tert-butyl-N-benzyl-1-naphthamide undergoes cyclisation to a tricyclic enolate which reacts diastereoselectively with electrophiles to give substituted 2,3,3a,9b-tetrahydro-1H-benzo[e]-isoindol-1-ones, the first example of an anionic cyclisation onto an aromatic ring.",

author = "Anjum Ahmed and Jonathan Clayden and Michael Rowley",

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AU - Clayden, Jonathan

AU - Rowley, Michael

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N2 - On treatment with ButLi and HMPA, N-tert-butyl-N-benzyl-1-naphthamide undergoes cyclisation to a tricyclic enolate which reacts diastereoselectively with electrophiles to give substituted 2,3,3a,9b-tetrahydro-1H-benzo[e]-isoindol-1-ones, the first example of an anionic cyclisation onto an aromatic ring.

AB - On treatment with ButLi and HMPA, N-tert-butyl-N-benzyl-1-naphthamide undergoes cyclisation to a tricyclic enolate which reacts diastereoselectively with electrophiles to give substituted 2,3,3a,9b-tetrahydro-1H-benzo[e]-isoindol-1-ones, the first example of an anionic cyclisation onto an aromatic ring.

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JO - Chemical Communications

JF - Chemical Communications

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Anionic cyclisations of an N-benzyl naphthamide: A route to benzo[e]isoindolones

Abstract

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