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

Autor:	Giovana S. Ramos, Marcelo Volpatto Marques, Marcus M. Sá, Adrielle P. Maximiano
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Cyclopropanation Organic Chemistry Epoxide Structural diversity Substrate (chemistry) Aldehyde Catalysis chemistry.chemical_compound chemistry Yield (chemistry) Wittig reaction Organic chemistry Phosphonium
Zdroj:	Synthesis. 53:2408-2421
ISSN:	1437-210X 0039-7881
DOI:	10.1055/a-1389-1203
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::45dbe9cc773a10b0db7707521809fd58 https://doi.org/10.1055/a-1389-1203 Zobrazit plný text záznamu