Synthesis of Sulfoximine Carbamates by Rhodium-Catalyzed Nitrene Transfer of Carbamates to Sulfoxides

Autor:	Robert Doran, James A. Bull, Marina Zenzola, Renzo Luisi
Rok vydání:	2015
Předmět:	Molecular Structure Methionine sulfoxide Nitrene Organic Chemistry Methionine Sulfoximine chemistry.chemical_element Catalysis Coupling reaction Rhodium chemistry.chemical_compound chemistry Sulfoxides Molecule Organic chemistry Carbamates
Zdroj:	The Journal of Organic Chemistry. 80:6391-6399
ISSN:	1520-6904 0022-3263
Popis:	Sulfoximines are of considerable interest for incorporation into medicinal compounds. A convenient synthesis of N-protected sulfoximines is achieved, under mild conditions, by rhodium-catalyzed transfer of carbamates to sulfoxides. The first examples of 4-membered thietane-oximines are prepared. Sulfoximines bearing Boc and Cbz groups are stable to further cross coupling reactions, and readily deprotected. This method may facilitate the preparation of NH-sulfoximines providing improved (global) deprotection strategies, which is illustrated in the synthesis of methionine sulfoxide (MSO).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0340acfd1728cedd83f455b7ece7c218 https://doi.org/10.1021/acs.joc.5b00844 Zobrazit plný text záznamu