Functionalized Cyclopropanes as Versatile Intermediates for the Diversity-Oriented Synthesis of γ-Lactones, γ-Lactams and δ-Lactams.

Autor: Maximiano, Adrielle P., Ramos, Giovana S., Marques, Marcelo V., Sá, Marcus M.
Předmět:
Zdroj: Synthesis; 2021, Vol. 53 Issue 14, p2408-2421, 14p
Abstrakt: A two-step procedure for the preparation of cyclopropanecarboxaldehyde-1,1-diester from a γ,δ-epoxyester and its synthetic versatility are described herein. The epoxide ring-opening/cyclopropanation process occurs in the presence of Mg(ClO4)2 under heating, resulting in cyclopropanemethanol-1,1-diester in 65% yield. A mild TEMPO-mediated oxidation of this substrate readily generated the corresponding aldehyde in 75% yield, which was applied in the one-pot synthesis of four cyclopropylidene-γ-lactams and three δ-lactams. In addition, vinylcyclopropanes were obtained through the Wittig reaction of the aldehyde with phosphonium salts and used as precursors for tetrahydrofurans. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index