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Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

ABSTRACT: Methods for the construction of quaternary carbon centers are of great interest to synthetic chemists due to their presence in natural products. Development of the Pd-catalyzed arylation of butenolides with high selectivity for the gamma-position allows for a facile construction of quaternary centers. The preparation of a wide variety of gamma-aryl butenolides containing a number of functional groups is outlined. An application of this chemistry for a one-pot synthesis of a tricyclic tetrahydroisoquinolinone is demonstrated.

SUBMITTER: Hyde AM

PROVIDER: S-EPMC2739656 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

Hyde Alan M AM Buchwald Stephen L SL

Organic letters 20090601 12

Methods for the construction of quaternary carbon centers are of great interest to synthetic chemists due to their presence in natural products. Development of the Pd-catalyzed arylation of butenolides with high selectivity for the gamma-position allows for a facile construction of quaternary centers. The preparation of a wide variety of gamma-aryl butenolides containing a number of functional groups is outlined. An application of this chemistry for a one-pot synthesis of a tricyclic tetrahydroi ...[more]

PMID: 19449882

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