Palladium-catalysed [π2a+π2s] cycloadditions of α-bromoalkyl ketenes to cyclopentadiene

Ian J.S. Fairlamb; Julia M. Dickinson; Ileana M. Cristea

doi:10.1016/S0040-4039(00)00478-0

Palladium-catalysed [π2a+π2s] cycloadditions of α-bromoalkyl ketenes to cyclopentadiene

Ian J.S. Fairlamb, Julia M. Dickinson, Ileana M. Cristea

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

7 Scopus citations

Abstract

7-Substituted bicyclo[3.2.0]hept-2-en-6-one derivatives were identified as intermediates towards biologically interesting compounds. An improved synthesis of 7-alkyl-7-bromobicyclo[3.2.0]hept-2-en-6-ones by palladium- catalysed [π2a+π2s] cycloaddition of α-bromoalkyl ketenes to cyclopentadiene is described. Increased yields and increasing exo alkyl cycloadducts were observed with various palladium catalysts under standard dehydrochlorination conditions. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	3739-3742
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(00)00478-0
State	Published - May 6 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Bicyclic aliphatic compounds
Cycloadditions
Ketenes
Palladium

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10.1016/S0040-4039(00)00478-0

Cite this

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title = "Palladium-catalysed [π2a+π2s] cycloadditions of α-bromoalkyl ketenes to cyclopentadiene",

abstract = "7-Substituted bicyclo[3.2.0]hept-2-en-6-one derivatives were identified as intermediates towards biologically interesting compounds. An improved synthesis of 7-alkyl-7-bromobicyclo[3.2.0]hept-2-en-6-ones by palladium- catalysed [π2a+π2s] cycloaddition of α-bromoalkyl ketenes to cyclopentadiene is described. Increased yields and increasing exo alkyl cycloadducts were observed with various palladium catalysts under standard dehydrochlorination conditions. (C) 2000 Elsevier Science Ltd.",

keywords = "Bicyclic aliphatic compounds, Cycloadditions, Ketenes, Palladium",

author = "Fairlamb, {Ian J.S.} and Dickinson, {Julia M.} and Cristea, {Ileana M.}",

note = "Funding Information: We would like to thank the Manchester Metropolitan University for a PhD scholarship to I.J.S.F. and the EEC for a TEMPUS grant for I.M.C.",

year = "2000",

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doi = "10.1016/S0040-4039(00)00478-0",

language = "English (US)",

volume = "41",

pages = "3739--3742",

journal = "Tetrahedron Letters",

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number = "19",

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TY - JOUR

T1 - Palladium-catalysed [π2a+π2s] cycloadditions of α-bromoalkyl ketenes to cyclopentadiene

AU - Fairlamb, Ian J.S.

AU - Dickinson, Julia M.

AU - Cristea, Ileana M.

N1 - Funding Information: We would like to thank the Manchester Metropolitan University for a PhD scholarship to I.J.S.F. and the EEC for a TEMPUS grant for I.M.C.

PY - 2000/5/6

Y1 - 2000/5/6

N2 - 7-Substituted bicyclo[3.2.0]hept-2-en-6-one derivatives were identified as intermediates towards biologically interesting compounds. An improved synthesis of 7-alkyl-7-bromobicyclo[3.2.0]hept-2-en-6-ones by palladium- catalysed [π2a+π2s] cycloaddition of α-bromoalkyl ketenes to cyclopentadiene is described. Increased yields and increasing exo alkyl cycloadducts were observed with various palladium catalysts under standard dehydrochlorination conditions. (C) 2000 Elsevier Science Ltd.

AB - 7-Substituted bicyclo[3.2.0]hept-2-en-6-one derivatives were identified as intermediates towards biologically interesting compounds. An improved synthesis of 7-alkyl-7-bromobicyclo[3.2.0]hept-2-en-6-ones by palladium- catalysed [π2a+π2s] cycloaddition of α-bromoalkyl ketenes to cyclopentadiene is described. Increased yields and increasing exo alkyl cycloadducts were observed with various palladium catalysts under standard dehydrochlorination conditions. (C) 2000 Elsevier Science Ltd.

KW - Bicyclic aliphatic compounds

KW - Cycloadditions

KW - Ketenes

KW - Palladium

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U2 - 10.1016/S0040-4039(00)00478-0

DO - 10.1016/S0040-4039(00)00478-0

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AN - SCOPUS:0034611967

SN - 0040-4039

VL - 41

SP - 3739

EP - 3742

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Palladium-catalysed [π2a+π2s] cycloadditions of α-bromoalkyl ketenes to cyclopentadiene

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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