Reaction of o-Oxazolinylphenyllithium with Carbon Monoxide. Carbonylative Cyclization via an Aroyllithium Intermediate
journal contributionposted on 21.10.2000, 00:00 by Keiji Iwamoto, Naoto Chatani, Shinji Murai
The carbonylation of a phenyllithium containing an oxazoline group at the ortho position, followed by quenching with water, afforded a tricyclic compound, 3,3-dimethyl-2,3-dihydrooxazolo[2,3-a]isoindol-5(9bH)-one, in 91% yield. This reaction proceeded via an intramolecular cyclization of the aroyllithium species, to give the tricyclic dienolate. Treatment of the tricyclic dienolate with electrophiles, such as alkyl halides, aldehydes, ketones, and epoxides gave the substituted oxazolo[2,3-a]isoindolinones in good yield.
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dimethylCarbon Monoxidealkyl halidesquenchingepoxidecarbonylationisoindolaldehydetricyclic compoundelectrophileoxazoloisoindolinoneortho positiontricyclic dienolateAroyllithium Intermediatephenyllithiumoxazoline groupOxazolinylphenyllithiumintramolecular cyclizationCarbonylative Cyclizationaroyllithium speciesketone