Efficient, enantioselective synthesis of a β,β-disubstituted carboxylic acid by Ru-XylPhanePhos-catalyzed asymmetric hydrogenation

Autor:	Christopher A. Teleha, Gabriela Alexandra Grasa, William A. Kinney, Antonio Zanotti-Gerosa, Shyamali Ghosh, Bruce E. Maryanoff
Rok vydání:	2008
Předmět:	chemistry.chemical_classification In situ Chemistry Stereochemistry Carboxylic acid Organic Chemistry Integrin antagonist Asymmetric hydrogenation Enantioselective synthesis Substrate (chemistry) Biochemistry Catalysis Drug Discovery Moiety
Zdroj:	Tetrahedron Letters. 49:5328-5331
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2008.06.068
Popis:	Enantioselective preparation of a key α v β 3 integrin antagonist intermediate was accomplished via catalytic asymmetric hydrogenation of the corresponding β,β-disubstituted α,β-unsaturated carboxylic acid bearing a 3-quinolinyl moiety. The successful application of a Ru-( R )-XylPhanePhos catalyst to this type of substrate is unprecedented. In situ NMR experiments of pre-catalyst formation/activation by CH 3 CO 2 H, and reaction parameter modification, revealed that [Ru(COD)(CF 3 CO 2 ) 2 ] 2 /( R )-XylPhanePhos is a highly active and efficient catalytic system.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e091ff7a55faf06ad933204637f60f75 https://doi.org/10.1016/j.tetlet.2008.06.068 Zobrazit plný text záznamu Full Text from ScienceDirect