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

Adrielle P. Maximiano; Giovana S. Ramos; Marcelo V. Marques; Marcus M. Sá

doi:10.1055/a-1389-1203

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(14): 2408-2421
DOI: 10.1055/a-1389-1203

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

Adrielle P. Maximiano

^aMESOLab (Laboratory of Methodology and Organic Synthesis), Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis-SC, Brazil

,

Giovana S. Ramos

^aMESOLab (Laboratory of Methodology and Organic Synthesis), Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis-SC, Brazil

,

Marcelo V. Marques

^bInstituto Federal Catarinense (IFC), Campus Fraiburgo, 89580-000 Fraiburgo-SC, Brazil

,

Marcus M. Sá∗

^aMESOLab (Laboratory of Methodology and Organic Synthesis), Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis-SC, Brazil

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

To Professor Albert J. Kascheres, in memoriam

Abstract

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.

Key words

γ,δ-epoxyester - cyclopropanecarboxaldehyde - lactonization - cyclopropylidene-γ-lactams - δ-lactams - one-pot process - structural diversity

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Referenzen

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