3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: an approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids

Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methylalkoxycarbonyl- and 3(2-Boc-aminoethyl)-alkox...

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Bibliographic Details
Published in:Tetrahedron 2015-12, Vol.71 (49), p.9313-9320
Main Authors: Paju, Anne, Kostomarova, Diana, Matkevitš, Katharina, Laos, Marit, Pehk, Tõnis, Kanger, Tõnis, Lopp, Margus
Format: Article
Language:English
Subjects:
3-Alkyl-1,2-diketones
3-Bromo-1,2-diketones
Homocitric acid
Lycoperdic acid
Negishi coupling
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Summary:Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methylalkoxycarbonyl- and 3(2-Boc-aminoethyl)-alkoxycarbonyl-1,2-cyclopentanediones—homocitric and lycoperdic acid precursors. Homocitric and lycoperdic acids were synthesized using asymmetric oxidation with the Ti(OiPr)4/tartaric ester/tBuOOH complex in two steps from the obtained precursors. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.10.014