Highly stereoselective formation of cis-enediones from α-diazo carbonyl compounds catalysed by [RuCl(η5-C5H5)(PPh3)2]

1997/01/01 by Walter Baratta, Alessandro Del Zotto · 4 citations
Chemistry · #Cyclopropane Reaction Mechanisms #Synthetic Organic Chemistry Methods #Synthesis and Catalytic Reactions

paper · doi:10.1039/a706459d

openalex publication_date 1997/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02

Abstract

Stereoselective decomposition of the α-diazo carbonyl compounds N2CHCOR [R = Me, Prn, Pri, (CH2)10CH3] catalysed by [RuCl(η5-C5H5)(PPh3)2] (0.1 mol%) in toluene at 65 °C affords quantitatively RCOCHCHCOR carbene dimers, the cis isomers being formed in 95–97% yield; under the same experimental conditions N2CHCOEt gives diethyl maleate in a purity of greater than 99%, the highest value for a stereoselective carbene–carbene dimer formation reported to date.

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