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Gold(I)-catalyzed synthesis of ?-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols.

ABSTRACT: Gold(I)-N-heterocyclic carbene (NHC) complexes proved to be a reliable catalytic system for the direct synthesis of functionalized ?-vinylbutyrolactones by intramolecular oxaallylic alkylation with primary alcohols. Good isolated chemical yields were obtained for a range of malonyl and acetate derivatives. The good performance in reagent-grade solvents and the functional group/moisture tolerance make this catalytic process a promising route for the synthesis of architecturally complex polycyclic structures.

SUBMITTER: Chiarucci M 

PROVIDER: S-EPMC3182428 | biostudies-other | 2011

REPOSITORIES: biostudies-other

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Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols.

Chiarucci Michel M   Locritani Mirko M   Cera Gianpiero G   Bandini Marco M  

Beilstein journal of organic chemistry 20110901

Gold(I)-N-heterocyclic carbene (NHC) complexes proved to be a reliable catalytic system for the direct synthesis of functionalized γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with primary alcohols. Good isolated chemical yields were obtained for a range of malonyl and acetate derivatives. The good performance in reagent-grade solvents and the functional group/moisture tolerance make this catalytic process a promising route for the synthesis of architecturally complex polycyclic  ...[more]