β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives

Jonathan Clayden; David W. Watson; Madeleine Helliwell; Mark Chambers

doi:10.1039/B308029C

β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives

Jonathan Clayden^*, David W. Watson, Madeleine Helliwell, Mark Chambers

^*Corresponding author for this work

School of Chemistry

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

35 Citations (Scopus)

Abstract

Substituted acrylamide derivatives of benzylamine are lithiated α to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a β-electron withdrawing group, 4-exo-trig cyclisation to a β-lactam.

Original language	English
Pages (from-to)	2582-2583
Number of pages	2
Journal	Chemical Communications
Volume	9
Issue number	20
Early online date	18 Sept 2003
DOIs	https://doi.org/10.1039/B308029C
Publication status	Published - 21 Oct 2003

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Organic & Biological

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title = "β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives",

abstract = "Substituted acrylamide derivatives of benzylamine are lithiated α to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a β-electron withdrawing group, 4-exo-trig cyclisation to a β-lactam.",

author = "Jonathan Clayden and Watson, \{David W.\} and Madeleine Helliwell and Mark Chambers",

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doi = "10.1039/B308029C",

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journal = "Chemical Communications",

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T1 - β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives

AU - Clayden, Jonathan

AU - Watson, David W.

AU - Helliwell, Madeleine

AU - Chambers, Mark

PY - 2003/10/21

Y1 - 2003/10/21

N2 - Substituted acrylamide derivatives of benzylamine are lithiated α to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a β-electron withdrawing group, 4-exo-trig cyclisation to a β-lactam.

AB - Substituted acrylamide derivatives of benzylamine are lithiated α to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a β-electron withdrawing group, 4-exo-trig cyclisation to a β-lactam.

UR - https://www.scopus.com/pages/publications/0142062462

U2 - 10.1039/B308029C

DO - 10.1039/B308029C

M3 - Article (Academic Journal)

AN - SCOPUS:0142062462

SN - 1359-7345

VL - 9

SP - 2582

EP - 2583

JO - Chemical Communications

JF - Chemical Communications

IS - 20

ER -

β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives

Abstract

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