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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Organic & Biological

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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",

year = "1998",

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doi = "10.1039/A707683E",

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journal = "Chemical Communications",

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T2 - A route to benzo[e]isoindolones

AU - Ahmed, Anjum

AU - Clayden, Jonathan

AU - Rowley, Michael

PY - 1998/2/7

Y1 - 1998/2/7

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.

UR - https://www.scopus.com/pages/publications/0000839710

U2 - 10.1039/A707683E

DO - 10.1039/A707683E

M3 - Article (Academic Journal)

AN - SCOPUS:0000839710

SN - 1359-7345

SP - 297

EP - 298

JO - Chemical Communications

JF - Chemical Communications

IS - 3

ER -

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

Abstract

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