n-Butyllithium-Induced Tandem [3,3]-Sigmatropic Rearrangement and Carbonyl Olefination of Allyl-1,1-dichlorovinyl Ethers

Autor:	Thomas G. Minehan, Aaron Christopher, Stephen Kelly, Dahniel Brandes
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Tandem chemistry Organic Chemistry medicine Dehydration Sigmatropic reaction n-Butyllithium medicine.disease Medicinal chemistry
Zdroj:	The Journal of Organic Chemistry. 86:17487-17495
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c02178
Popis:	Exposure of dichlorovinyl ethers 1 to n-butyllithium and addition of saturated or unsaturated aldehydes, ketones, or esters at ambient temperature furnishes rearranged α,β-unsaturated carboxylic acids, isolated as their corresponding methyl esters 2 in 48-91% overall yields. Exposure of dichlorovinyl ethers 1 to n-butyllithium, addition of aldehydes, ketones, dialdehydes, or diketones at -78 °C, and warming to 80 °C in the presence of SiO2 provide 1,4-dienes 3 or cycloalken-1-ols (or their dehydration products) 4 in 45-72% overall yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::65e32bb7e0ed4f8bfaee42a45eaf8cd7 https://doi.org/10.1021/acs.joc.1c02178 Zobrazit plný text záznamu