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Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium-Catalyzed Alkyne Cyclotrimerizations.

ABSTRACT: (Cyclooctadiene)(pentamethylcyclopentadiene)ruthenium chloride [Cp*RuCl(cod)] has been used to catalyze the regioselective cyclization of amide-tethered diynes with monosubstituted alkynes to give polysubstituted isoindolinones. Notably, the presence of a trimethylsilyl group on the diyne generally led to complete control over the regioselectivity of the alkyne cyclotrimerization. The cyclization reaction worked well in a sustainable non-chlorinated solvent and was tolerant of moisture. The optimized conditions were effective with a diverse range of alkynes and diynes. The 7-silylisoindolinone products could be halogenated, protodesilylated or ring opened to access a range of usefully functionalized products.

SUBMITTER: Foster RW

PROVIDER: S-EPMC3793232 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Highly Regioselective Synthesis of Substituted Isoindolinones <i>via</i> Ruthenium-Catalyzed Alkyne Cyclotrimerizations.

Foster Robert W RW Tame Christopher J CJ Hailes Helen C HC Sheppard Tom D TD

Advanced synthesis & catalysis 20130801 11-12

(Cyclooctadiene)(pentamethylcyclopentadiene)ruthenium chloride [Cp*RuCl(cod)] has been used to catalyze the regioselective cyclization of amide-tethered diynes with monosubstituted alkynes to give polysubstituted isoindolinones. Notably, the presence of a trimethylsilyl group on the diyne generally led to complete control over the regioselectivity of the alkyne cyclotrimerization. The cyclization reaction worked well in a sustainable non-chlorinated solvent and was tolerant of moisture. The opti ...[more]

PMID: 24124414

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