4.6 Article

Efficient tandem process for the catalytic deprotection of N-allyl amides and lactams in aqueous media:: A novel application of the bis(allyl)ruthenium(IV) catalysts [Ru(η3:η2:η3-C12H18)Cl2] and [{Ru(η3:η3-C10H16)-(μ-Cl)Cl}2]

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 13, 期 23, 页码 6590-6594

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700477

关键词

allylic compounds; amides; aqueous-phase catalysis; lactams; protecting groups; ruthenium

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An operationally simple and highly efficient methodology for the removal of the allyl protecting group in amides and lactams has been developed by using the commercially available bis(allyl)-ruthenium(IV) catalysts [Ru(eta(3):eta(3):eta(3)-C12H18)Cl-2] (C12H18=dodeca-2,6,10-triene-1,12-diyl) and [{Ru(eta(3):eta(3)-C10H16)mu- Cl)Cl}(2)] (C10H18=2,7-dimethylocta-2,6-diene-1,8-diyl). The tandem process, which takes place in aqueous media and proceeds in a one-pot manner, involves the initial isomerization of the C = C bond of the allyl unit and subsequent oxidative cleavage of the resulting enamide.

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