Stereoselective Rh-Catalyzed Hydrogenative Desymmetrization of Achiral Substituted 1,4-Dienes
作者： Héctor Fernández-Pérez , Joan R. Lao , Anton Vidal-Ferran
DOI: 10.1021/ACS.ORGLETT.6B01088
关键词:
摘要: Highly efficient catalytic stereoselective hydrogenative desymmetrization reactions mediated by rhodium complexes derived from enantiopure phosphine–phosphite (P–OP) ligands are described. The highest performing ligand, which contains a TADDOL-derived phosphite fragment [TADDOL = (2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)], presented excellent properties for the of set achiral 1,4-dienes, providing access to selective formation variety enantioenriched secondary and tertiary alcohols (six examples, up 92% ee).
acs.org
sci-hub.se 参考文章(28)
José Luis Núñez-Rico, Héctor Fernández-Pérez, Anton Vidal-Ferran, Asymmetric hydrogenation of unprotected indoles using iridium complexes derived from P–OP ligands and (reusable) Brønsted acids Green Chemistry. ,vol. 16, pp. 1153- 1157 ,(2014) , 10.1039/C3GC42132E
Sang-Jin Jeon, Hongmei Li, Celina García, Lynne K. LaRochelle, Patrick J. Walsh, Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones. Journal of Organic Chemistry. ,vol. 70, pp. 448- 455 ,(2005) , 10.1021/JO048683E
Anna Falk, Alberto Cavalieri, Gary S. Nichol, Dieter Vogt, Hans-Günther Schmalz, Enantioselective Nickel-Catalyzed Hydrocyanation using Chiral Phosphine-Phosphite Ligands: Recent Improvements and Insights Advanced Synthesis & Catalysis. ,vol. 357, pp. 3317- 3320 ,(2015) , 10.1002/ADSC.201500644
Pablo Etayo, José Luis Núñez-Rico, Héctor Fernández-Pérez, Anton Vidal-Ferran, Enantioselective access to chiral drugs by using asymmetric hydrogenation catalyzed by Rh(P-OP) complexes. Chemistry: A European Journal. ,vol. 17, pp. 13978- 13982 ,(2011) , 10.1002/CHEM.201103014
Michał Rachwalski, Niek Vermue, Floris P. J. T. Rutjes, Recent advances in enzymatic and chemical deracemisation of racemic compounds Chemical Society Reviews. ,vol. 42, pp. 9268- 9282 ,(2013) , 10.1039/C3CS60175G
Héctor Fernández-Pérez, Jordi Benet-Buchholz, Anton Vidal-Ferran, Enantiopure narrow bite-angle P-OP ligands: synthesis and catalytic performance in asymmetric hydroformylations and hydrogenations. Chemistry: A European Journal. ,vol. 20, pp. 15375- 15384 ,(2014) , 10.1002/CHEM.201404731
Héctor Fernández-Pérez, Steven M. A. Donald, Ian J. Munslow, Jordi Benet-Buchholz, Feliu Maseras, Anton Vidal-Ferran, Highly modular P-OP ligands for asymmetric hydrogenation: synthesis, catalytic activity, and mechanism. Chemistry: A European Journal. ,vol. 16, pp. 6495- 6508 ,(2010) , 10.1002/CHEM.200902915
Joan R. Lao, J. Benet-Buchholz, Anton Vidal-Ferran, 1,1-P–OP Ligands with P-Stereogenic Phosphino Groups in Asymmetric Hydrogenations and Hydroformylations Organometallics. ,vol. 33, pp. 2960- 2963 ,(2014) , 10.1021/OM500378B
José L. Núñez-Rico, Héctor Fernández-Pérez, J. Benet-Buchholz, Anton Vidal-Ferran, Asymmetric Hydrogenation of Heteroaromatic Compounds Mediated by Iridium-(P-OP) Complexes Organometallics. ,vol. 29, pp. 6627- 6631 ,(2010) , 10.1021/OM100955T
Anton Vidal-Ferran, Bugga Balakrishna, A Practical Synthesis of Rhodium Precatalysts for Enantioselective Hydrogenative Transformations Synthesis. ,vol. 48, pp. 997- 1001 ,(2016) , 10.1055/S-0035-1561360