Highly enantioselective synthesis of alpha,beta-diaminopropanoic acid derivatives using a catalytic asymmetric hydrogenation approach

Autor:	Chin Yu Lim, Hui-Yin Li, P. Ma, Linnan He, Andrea J. Robinson
Rok vydání:	2001
Předmět:	Steric effects Olefin fiber Chemistry Stereochemistry Organic Chemistry Asymmetric hydrogenation Enantioselective synthesis Carbon-13 NMR Catalysis Metal chemistry.chemical_compound visual_art visual_art.visual_art_medium Carboxylate
Zdroj:	The Journal of organic chemistry. 66(12)
ISSN:	0022-3263
Popis:	Rh-DuPhos-catalyzed asymmetric hydrogenation of alpha,beta-diamidoacrylates provides a highly efficient and enantioselective route to chiral alpha,beta-diaminopropanoic acid derivatives. The mechanistic course of the hydrogenation was studied using isotopically enriched enamide complexes and phosphorus and carbon NMR. Addition of methyl alpha-N-benzoyl-beta-N-acetyl-diaminopropenoate to the solvated catalyst gave a single 1:1 enamide complex and demonstrated the binding of the olefin and alpha-amide carbonyl group; the carboxylate and beta-N-acyl groups did not bind to the metal. Changes to the electronic and steric properties of the beta-N-acyl group were well tolerated; however, small changes to the binding alpha-N-acyl group were found to significantly affect hydrogenation yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::443009881a26af638c441c676d7873a5 https://pubmed.ncbi.nlm.nih.gov/11397145 Zobrazit plný text záznamu