A New Reaction Manifold for the Barton Radical Intermediates: Synthesis of N-Heterocyclic Furanosides and Pyranosides via the Formation of the C1−C2 Bond

Autor:	T. V. RajanBabu, Brian I. Bliss, Jong Uk Rhee
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Stereochemistry Hydride Substituent Free-radical reaction Hydrazone General Chemistry Biochemistry Medicinal chemistry Radical cyclization Acceptor Catalysis chemistry.chemical_compound Colloid and Surface Chemistry chemistry Organic synthesis Deoxygenation
Zdroj:	Journal of the American Chemical Society. 125:1492-1493
ISSN:	1520-5126 0002-7863
Popis:	The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl- or exo-hept-6-enyl-type radical cyclization when a suitable radical acceptor (e.g., alpha,beta-unsaturated ester, oxime ether, or hydrazone) is appropriately placed. Carbohydrate-derived imidazolyl and triazolyl thiourethanes with such acceptors, upon addition to excess of a good hydride donor (reverse addition), undergo efficient cyclization reactions to give N-heterocyclic furanosides, and, surprisingly even N-pyranosides. Depending on the acceptor, glycosides with either a C(2)()-amino or a C(2)()-carbon substituent are formed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f47c72e1f150d4a431683c66c8503916 https://doi.org/10.1021/ja028617z Zobrazit plný text záznamu