A Formal [4 + 4] Complementary Ambiphile Pairing Reaction: A New Cyclization Pathway for ortho-Quinone Methides

Autor:	Thiwanka Bandara Samarakoon, Moon Young Hur, Ryan D. Kurtz, Paul R. Hanson
Rok vydání:	2010
Předmět:	Models Molecular Molecular Structure Stereochemistry Chemistry Organic Chemistry Synthon Stereoisomerism Crystallography X-Ray Biochemistry Article Quinone Indolequinones Cyclization Pairing Molecule Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 12:2182-2185
ISSN:	1523-7052 1523-7060
Popis:	A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::519be57ae505b1c6f24cf75d75e407ab https://doi.org/10.1021/ol100495w Zobrazit plný text záznamu