Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts?
Chemical Communications Pub Date: 2021-04-07 DOI: 10.1039/D1CC00663K
Abstract
The highly enantioselective copper-catalyzed propargylic amination of propargylic esters with amine hydrochloride salts has been realized for the first time using copper salts with chiral N,N,P-ligands. This method features a broad substrate scope and wide functional group tolerance, generating propargylic amines in good to excellent yields with high enantioselectivities (up to 99% ee). The utility of the approach was demonstrated by late-stage functionalization of marketed pharmaceuticals.
Recommended Literature
- [1] An atomically efficient, highly stable and redox active Ce0.5Tb0.5Ox (3% mol.)/MgO catalyst for total oxidation of methane? Juan J. Sánchez,Miguel López-Haro,Juan C. Hernández-Garrido,Ginesa Blanco,Miguel A. Cauqui,José M. Rodríguez-Izquierdo,José A. Pérez-Omil,José J. Calvino,María P. YesteJ. Mater. Chem. A, 2019,7, 8993-9003 10.1039/C8TA11672E
- [2] An amplified fluorescence detection of T4 polynucleotide kinase activity based on coupled exonuclease III reaction and a graphene oxide platform? Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao YouAnalyst, 2015,140, 1827-1831 10.1039/C4AN01953A
- [3] An antimonate pyrochlore (H1.23Sr0.45SbO3.48) for photocatalytic oxidation of benzene: effective oxygen usage and excellent activity? Jing Chen,Yu Shao,Danzhen LiJ. Mater. Chem. A, 2017,5, 937-941 10.1039/C6TA08652G
- [4] An atomistic mechanism for the degradation of perovskite solar cells by trapped charge? Eunhak Lim,Jiyoung Heo,Seong Keun KimNanoscale, 2019,11, 11369-11378 10.1039/C9NR02193K
- [5] An astrophysically-relevant mechanism for amino acid enantiomer enrichment Stephen P. Fletcher,Richard B. C. Jagt,Ben L. FeringaChem. Commun., 2007, 2578-2580 10.1039/B702882B
- [6] An intramolecular tryptophan-condensation approach for peptide stapling? Eunice Y.-L. Hui,Bhimsen Rout,Yaw Sing Tan,Kok-Ping Chan,Charles W. JohannesOrg. Biomol. Chem., 2018,16, 389-392 10.1039/C7OB02667F
- [7] Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. BudaPhys. Chem. Chem. Phys., 2011,13, 10270-10279 10.1039/C1CP20213H
- [8] An artificial CO-releasing metalloprotein built by histidine-selective metallation? Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?oChem. Commun., 2015,51, 3993-3996 10.1039/C4CC10204E
- [9] An investigation of new infrared nonlinear optical material: BaCdSnSe4, and three new related centrosymmetric compounds: Ba2SnSe4, Mg2GeSe4, and Ba2Ge2S6? Kui Wu,Zhihua Yang,Shilie PanDalton Trans., 2015,44, 19856-19864 10.1039/C5DT03215F
- [10] Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties? S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. LeeRSC Adv., 2014,4, 23107-23115 10.1039/C4RA02318H
Journal Name:Chemical Communications
research_products
-
CAS no.: 89640-58-4