Direct Synthesis of Chiral 3-Arylsuccinimides by Rhodium-Catalyzed Enantioselective Conjugate Addition of Arylboronic Acids to Maleimides

Autor:	Balraj Gopula, Julian P. Henschke, Ping Yu Wu, Jen-Chieh Hsieh, Hsyueh Liang Wu, Shu Han Yang, Ting Shen Kuo
Rok vydání:	2015
Předmět:	Pyrrolidines Bicyclic molecule Diene Organic Chemistry Enantioselective synthesis Succinimides chemistry.chemical_element Stereoisomerism General Chemistry Ligands Boronic Acids Catalysis Pyrrolidine Adduct Rhodium Maleimides chemistry.chemical_compound chemistry Organic chemistry Conjugate
Zdroj:	Chemistry - A European Journal. 21:11050-11055
ISSN:	0947-6539
Popis:	Chiral rhodium catalysts comprising 2,5-diaryl- substituted bicyclo[2.2.1]diene ligands L1-L10 were utilized in the enantioselective 1,4-addition reaction of arylboronic acids to N-substituted maleimides. In the presence of 2.5 mol % of Rh(I) /L2, enantioenriched conjugate addition adducts were isolated in 72-99 % yields with 86-98 % ee. This protocol offers a convenient method to access a variety of 3-arylsuccinimides in a highly enantioselective manner. Maleimides with readily cleavable N-protecting groups were tolerated enabling the synthesis of useful synthetic intermediates. Pyrrolidine 4, a biologically active compound, and pyrrolidine 5, an ent-precursor to an HSD-1 inhibitor, were synthesized to demonstrate the utility of this method.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1a0d8e5be2f8feb05c107cf1e9af8f0c https://doi.org/10.1002/chem.201501059 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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