Copper-Catalyzed Three-Component Carboiminolactonization of Electron-Deficient Olefins.

Autor: Wendlandt HC; Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States., Trammel GL; Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States., Kohler DG; Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States., Utley JA; Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States., Nicely AM; Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States., Popov AG; Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States., Hull KL; Department of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas 78712, United States.; Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Feb 02; Vol. 89 (3), pp. 2024-2031. Date of Electronic Publication: 2024 Jan 10.
DOI: 10.1021/acs.joc.3c02326
Abstrakt: Herein we report the three-component copper-catalyzed carboiminolactonization of α,β-unsaturated carbonyl derivatives. In the presence of a Cu(I) catalyst, α-haloesters, electron-deficient alkenes, and primary amines couple to generate γ-iminolactones in a single step. The scope of the reaction is explored with respect to the three coupling partners. Nineteen examples are presented with yields of these hydrolytically labile heterocycles of up to 69%. Mechanistic investigations support the formation of an oxocarbenium by way of an atom transfer radical addition (ATRA) intermediate.
Databáze: MEDLINE
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