Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade (C3) Sequences: Scope, Limitation, and Computational Investigations

Autor:	Paul Wendelboe, Erica L. Woodall, Chunyin M. Law, Christian R. Zwick, Riley H. Kaufman, John R. Goodell, T. Andrew Mitchell, Christopher G. Hamaker, Justin A. Simanis, Henry B. Wedler, Dean J. Tantillo
Rok vydání:	2018
Předmět:	chemistry.chemical_classification Scope (project management) 010405 organic chemistry Alkene Organic Chemistry Scope limitation 010402 general chemistry 01 natural sciences Combinatorial chemistry Cycloaddition 0104 chemical sciences chemistry Cascade Intramolecular force Conjugate
Zdroj:	The Journal of Organic Chemistry. 83:9818-9838
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.8b01322
Popis:	Oxidopyrylium-alkene [5 + 2] cycloaddition conjugate addition cascade (C3) sequences are described. Intramolecular cycloadditions involving terminal alkenes, enals, and enones were investigated. Substrates with tethers of varying lengths delivered five- and six-membered carbocycles and heterocycles thus demonstrating the scope and limitation of the cycloaddition–conjugate addition cascade. Several experiments and theoretical calculations provide evidence for the proposed mechanistic pathway.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::67b4ce3b697cadef93db16ba633b75d6 https://doi.org/10.1021/acs.joc.8b01322 Zobrazit plný text záznamu