Organocatalytic Enantioselective Synthesis of Polysubstituted Spirooxindoles using a Tandem Michael-Michael Reaction

Autor:	Nirmal K. Rana, Hadi D. Arman, Naresh Ramireddy, Santhi Abbaraju, John C.-G. Zhao
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Thiourea chemistry Cascade reaction Tandem Organocatalysis Enantioselective synthesis Michael reaction Organic chemistry Stereoselectivity General Chemistry Stereocenter
Zdroj:	Advanced Synthesis & Catalysis. 357:2633-2638
ISSN:	1615-4150
Popis:	A highly efficient stereoselective method for the synthesis of functionalized spirooxindole derivatives with four contiguous stereogenic centers, including two adjacent quaternary stereogenic centers, was realized through an organocatalytic tandem Michael–Michael reaction. By employing a quinidine-derived thiourea organocatalyst, the reaction between (E)-2-cyano-2-(2-oxo-1-tritylindolin-3-ylidene)acetates and (E)-1-alkyl-6-nitro-hex-2-en-1-ones yields the desired spirooxindole products in good yields (up to 90%) and with excellent stereoselectivities (up to 95:5 dr and 98% ee).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4e4116d3b77ded381fd0a99e0c0827dd https://doi.org/10.1002/adsc.201500298 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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