One-pot synthesis of 2-methylfurans from 3-(trimethylsilyl)propargyl acetates promoted by trimethylsilyl trifluoromethanesulfonate

Autor:	Alex V. Helbling, Danielle E. Sklar, Yiqi Liu, C. Wade Downey
Rok vydání:	2021
Předmět:	Substitution reaction Trimethylsilyl Organic Chemistry One-pot synthesis Alkylation Biochemistry Medicinal chemistry chemistry.chemical_compound Trimethylsilyl trifluoromethanesulfonate chemistry Drug Discovery Propargyl Triethylamine Triflic acid
Zdroj:	Tetrahedron Letters. 87:153424
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2021.153424
Popis:	In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine, 3-(trimethylsilyl)propargyl carboxylates undergo a one-pot alkylation-cyclization-desilylation reaction with ketones to produce 2-methylfurans. Alkylation at 0 °C in methylene chloride, followed by acid-catalyzed cyclization at room temperature, provides the furans in 52-86% yield. Cyclization and desilylation appear to be promoted by triflic acid generated in situ from the exposure of the reaction mixture to water upon completion of the initial substitution reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::75723567fe0db32016a5da227579fa5b https://doi.org/10.1016/j.tetlet.2021.153424 Zobrazit plný text záznamu Full Text from ScienceDirect