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Synthesis 2021; 53(14): 2408-2421
DOI: 10.1055/a-1389-1203
DOI: 10.1055/a-1389-1203
feature
Functionalized Cyclopropanes as Versatile Intermediates for the Diversity-Oriented Synthesis of γ-Lactones, γ-Lactams and δ-Lactams
The authors are grateful to the Brazilian governmental agencies CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior), CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico) and FAPESC (Fundação de Amparo à Pesquisa do Estado de Santa Catarina) for fellowships. Support from INCT-Catálise/FAPESC/ CNPq/CAPES (Instituto Nacional de Ciência e Tecnologia Catálise em Sistemas Moleculares e Nanoestruturados) is also gratefully acknowledged.
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 diversitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1389-1203.
- Supporting Information
Publication History
Received: 30 November 2020
Accepted after revision: 11 February 2021
Accepted Manuscript online:
11 February 2021
Article published online:
09 March 2021
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