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

Author(s)

Lima, Samia R. ^[1] ; Coelho, Fernando ^[1]

Affiliation

^[1] Univ Estadual Campinas, Lab Synth Nat Prod & Drugs, Inst Chem, BR-13083970 Campinas, SP - Brazil

• Document type: Journal article
• Source: ACS OMEGA; v. 5, n. 14, p. 8032-8045, APR 14 2020.
• Web of Science Citations: 0

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 alpha-alkylidene-gamma-lactones upon reduction with sodium borohydride. In the course of the scope evaluation, we discovered that this methodology could also furnish alpha-arylidene-beta,gamma-butenolides. (AU)

• FAPESP's process: 18/02611-0 - Post-Functionalization of Small Ply-functionalized Molecules: A Robust Approach to the Synthesis of New Structural Patterns with POtential Biological Activity
• Grantee: Fernando Antonio Santos Coelho
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC