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Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of ?-Arylidene-butyrolactones.

ABSTRACT: We report a direct, straightforward, and regioselective hydration of 1,4-enynes designed from Morita-Baylis-Hillman adducts. Under smooth conditions and short reaction times, gold-catalyzed hydration of internal alkynes provides synthetically useful ketones as single regioisomers in yields higher than 90%. The synthetic usefulness of this protocol was demonstrated by the conversion of selected ketones into biologically valuable ?-alkylidene-?-lactones upon reduction with sodium borohydride. In the course of the scope evaluation, we discovered that this methodology could also furnish ?-arylidene-?,?-butenolides.

SUBMITTER: Lima SR 

PROVIDER: S-EPMC7161055 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of α-Arylidene-butyrolactones.

Lima Samia R SR   Coelho Fernando F  

ACS omega 20200401 14

We report a direct, straightforward, and regioselective hydration of 1,4-enynes designed from Morita-Baylis-Hillman adducts. Under smooth conditions and short reaction times, gold-catalyzed hydration of internal alkynes provides synthetically useful ketones as single regioisomers in yields higher than 90%. The synthetic usefulness of this protocol was demonstrated by the conversion of selected ketones into biologically valuable α-alkylidene-γ-lactones upon reduction with sodium borohydride. In t  ...[more]

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