1,4-pentadienyl-3-sulfonamides: Frameworks for disfavored radical cascade cyclizations

Sacha Bommezijn; Concepcion Gonzalez Martin; Alan R. Kennedy; Dimitrios Lizos; John A. Murphy

doi:10.1021/ol0166449

1,4-pentadienyl-3-sulfonamides: Frameworks for disfavored radical cascade cyclizations

Sacha Bommezijn, Concepcion Gonzalez Martin, Alan R. Kennedy, Dimitrios Lizos, John A. Murphy

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

1,4-Pentadienyl-3-sulfonamides afford products including those resulting from disfavored 5-endo-trig reactions when subjected to radical cyclization conditions. Products resulting from pathways featuring 4-exo-trig cyclizations are also detected, even when the 4-exo-trig reaction leads to a highly strained bicyclo[3.2.0] ring system.

Original language	English
Pages (from-to)	3405-3407
Number of pages	2
Journal	Organic Letters
Volume	3
Issue number	21
DOIs	https://doi.org/10.1021/ol0166449
Publication status	Published - 21 Sept 2001

Keywords

1
4-Pentadienyl-3-sulfonamides
5-endo-trig reactions
4-exo-trig cyclizations
ring system

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10.1021/ol0166449

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title = "1,4-pentadienyl-3-sulfonamides: Frameworks for disfavored radical cascade cyclizations",

abstract = "1,4-Pentadienyl-3-sulfonamides afford products including those resulting from disfavored 5-endo-trig reactions when subjected to radical cyclization conditions. Products resulting from pathways featuring 4-exo-trig cyclizations are also detected, even when the 4-exo-trig reaction leads to a highly strained bicyclo[3.2.0] ring system.",

keywords = "1, 4-Pentadienyl-3-sulfonamides, 5-endo-trig reactions, 4-exo-trig cyclizations, ring system",

author = "Sacha Bommezijn and Martin, {Concepcion Gonzalez} and Kennedy, {Alan R.} and Dimitrios Lizos and Murphy, {John A.}",

year = "2001",

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doi = "10.1021/ol0166449",

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T1 - 1,4-pentadienyl-3-sulfonamides: Frameworks for disfavored radical cascade cyclizations

AU - Bommezijn, Sacha

AU - Martin, Concepcion Gonzalez

AU - Kennedy, Alan R.

AU - Lizos, Dimitrios

AU - Murphy, John A.

PY - 2001/9/21

Y1 - 2001/9/21

N2 - 1,4-Pentadienyl-3-sulfonamides afford products including those resulting from disfavored 5-endo-trig reactions when subjected to radical cyclization conditions. Products resulting from pathways featuring 4-exo-trig cyclizations are also detected, even when the 4-exo-trig reaction leads to a highly strained bicyclo[3.2.0] ring system.

AB - 1,4-Pentadienyl-3-sulfonamides afford products including those resulting from disfavored 5-endo-trig reactions when subjected to radical cyclization conditions. Products resulting from pathways featuring 4-exo-trig cyclizations are also detected, even when the 4-exo-trig reaction leads to a highly strained bicyclo[3.2.0] ring system.

KW - 1

KW - 4-Pentadienyl-3-sulfonamides

KW - 5-endo-trig reactions

KW - 4-exo-trig cyclizations

KW - ring system

UR - http://dx.doi.org/10.1021/ol0166449

U2 - 10.1021/ol0166449

DO - 10.1021/ol0166449

M3 - Article

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EP - 3407

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

1,4-pentadienyl-3-sulfonamides: Frameworks for disfavored radical cascade cyclizations

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1,4-pentadienyl-3-sulfonamides: Frameworks for disfavored radical cascade cyclizations

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