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-Science-Chemical Encyclopedia-lookchem

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
Add time:07/16/2019 Source:sciencedirect.com

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.

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