A New 1-Alkoxy-2-(chalcogeno)allylic or 1-Alkoxy-2,4-bis(chalcogeno)penta-2,4-dienyl Cation: Highly-Regioselective Allylating or Penta-2,4-dienylating Electrophiles and Their Reactions

Autor:	Mitsuhiro Yoshimatsu, Motonori Komori, Satoshi Gotoh, Kazunari Ikeda
Rok vydání:	1998
Předmět:	chemistry.chemical_compound Allylic rearrangement chemistry Nucleophile Organic Chemistry Acetal Electrophile Intramolecular cyclization Alkoxy group Regioselectivity Medicinal chemistry Adduct
Zdroj:	The Journal of Organic Chemistry. 63:6619-6624
ISSN:	1520-6904 0022-3263
Popis:	2-(Chalcogeno)-1-ethoxyallylic cations 4A are easily generated from the reactions of 2-(chalcogeno)-1-ethoxyprop-1-en-3-ols 2a−e or 2-(chalcogeno)prop-2-enal acetals 3a−c and TMSOTf and reacted with various nucleophiles to give the adducts 5a−8a, 5b−11b, and 5c−e regio and stereoselectively. 2,4-Bis(chalcogeno)penta-2,4-dienal acetals 16a,c and the 2,4,6-tris(phenylthio)hepta-2,4,6-trienal acetal 20c also gave the dienones 17a,c and 21c in good yields. Furthermore, the intramolecular cyclization of the alkenyl alcohols 25a,b and the 2,4-dienal 2,4-dinitrophenyl hydrazones 29a−c afforded the tetrahydrofurans 26a,b and 3,5-bis(chalcogeno)pyridines 30a−c, respectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b548fa606378c578f68fcc43e12d1014 https://doi.org/10.1021/jo9807767 Zobrazit plný text záznamu