Palladium catalysed reactions of allene with active methylene pronucleophiles. C-1,3-Dienylmethyl derivatives and their Diels–Alder reactions

A 2-step 100% atom economic sequence is reported whereby active methylene pronucleophiles react with 2 mol equiv. of allene to give bis-1,3-dienylmethyl derivatives of the pronucleophiles. Subsequent double Diels–Alder reactions furnish 1,1′-linked cyclohexenes with a 3-carbon spacer. Graphic

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 44; pp. 9187 - 9197
Main Authors Grigg, Ronald, Kongathip, Ngampong, Kongathip, Boonsang, Luangkamin, Suwaporn, Dondas, H.Ali
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.10.2001
Elsevier
Subjects
allene dimerisation
atom economy
bis-allylation
Chemistry
Chemistry, Organic
chromans
Physical Sciences
Science & Technology
π-allylpalladium (II) species
atom economy
bis-allylation
allene dimerisation
π-allylpalladium (II) species
chromans
NUCLEOPHILES
CARBON-MONOXIDE
pi-allylpalladium (II) species
HYDROFORMYLATION
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Summary:A 2-step 100% atom economic sequence is reported whereby active methylene pronucleophiles react with 2 mol equiv. of allene to give bis-1,3-dienylmethyl derivatives of the pronucleophiles. Subsequent double Diels–Alder reactions furnish 1,1′-linked cyclohexenes with a 3-carbon spacer. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00924-3