Arylsulfonyl Groups: The Best Cyclization Auxiliaries for the Preparation of ATRC γ-Lactams can be Acidolytically Removed

Autor:	Maria Cristina Menziani, Andrea Cornia, Armando Gennaro, Abdirisak Ahmed Isse, Domenico Spinelli, Franco Ghelfi, Fabrizio Roncaglia, Francesco Muniz-Miranda, Andrew J. Clark, Fulvia Felluga
Rok vydání:	2014
Předmět:	Sulfonyl chemistry.chemical_classification Stereochemistry Radical Organic Chemistry Redox cycle Substituent Ring (chemistry) Radical cyclization Combinatorial chemistry chemistry.chemical_compound chemistry Halogen Aromatic moiety Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2014:6734-6745
ISSN:	1434-193X
Popis:	The N-arylsulfonyl group, which is the best and most useful cyclization auxiliary for the transition-metal-catalyzed atom transfer radical cyclization (ATRC) of N-allyl-α-polychloroamides, can be effectively removed from the target γ-lactams by using H2SO4–HOAc, without impairing the halogen functions. The reaction involves H+ attack on the aromatic moiety, and is strongly responsive to the electronic properties of the substituent bound to the aromatic ring: electron-donating groups, such as methyl or methoxy are, in fact, required for efficient “deprotection”. The N-p-nitrophenylsulfonyl cyclization auxiliary, in contrast to all the other sulfonyl groups tested, proved to be unsuitable for the ATRC, owing to a side reductive transposition that halts the redox cycle.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::42415eecdcce110ab3fccb23279a2469 https://doi.org/10.1002/ejoc.201402769 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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