Highly enantioselective Rh-catalysed hydrogenation of 1-alkyl vinyl esters using phosphine-phosphoramidite ligands.
作者： Tina Maria Konrad , Pascal Schmitz , Walter Leitner , Giancarlo Franciò
关键词:
摘要: MatPhos, a good mate for hard tasks: The asymmetric hydrogenation of 1-alkyl vinyl esters, thwarted so far by mediocre ee values and low activities, can now be achieved with MatPhos/Rh catalysts 96-99% variety substrates at catalyst loadings (0.1-1 mol %) under mild conditions (5-20 bar H2, room temperature). After hydrolysis, the corresponding chiral secondary alkyl alcohols obtained in high enantiopurities providing general practical route to this important product class.
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Takeshi Ohkuma, Masatoshi Koizumi, Kilian Muñiz, Gerhard Hilt, Chizuko Kabuto, Ryoji Noyori, trans-RuH(η1-BH4)(binap)(1,2-diamine): A Catalyst for Asymmetric Hydrogenation of Simple Ketones under Base-Free Conditions Journal of the American Chemical Society. ,vol. 124, pp. 6508- 6509 ,(2002) , 10.1021/JA026136+
Giancarlo Franciò, Felice Faraone, Walter Leitner, Asymmetric Catalysis with Chiral Phosphane/Phosphoramidite Ligands Derived from Quinoline (QUINAPHOS) Angewandte Chemie International Edition. ,vol. 39, pp. 1428- 1430 ,(2000) , 10.1002/(SICI)1521-3773(20000417)39:8<1428::AID-ANIE1428>3.0.CO;2-K
Qiongzhong Jiang, Dengming Xiao, Zhaoguo Zhang, Ping Cao, Xumu Zhang, Highly Enantioselective Hydrogenation of Cyclic Enol Acetates Catalyzed by a Rh-PennPhos Complex Angewandte Chemie International Edition. ,vol. 38, pp. 516- 518 ,(1999) , 10.1002/(SICI)1521-3773(19990215)38:4<516::AID-ANIE516>3.0.CO;2-B
Timothy W. Liwosz, Sherry R. Chemler, Copper-Catalyzed Enantioselective Intramolecular Alkene Amination/Intermolecular Heck-Type Coupling Cascade Journal of the American Chemical Society. ,vol. 134, pp. 2020- 2023 ,(2012) , 10.1021/JA211272V
Neil W Boaz, Asymmetric hydrogenation of acyclic enol esters Tetrahedron Letters. ,vol. 39, pp. 5505- 5508 ,(1998) , 10.1016/S0040-4039(98)00730-8
Simon Burk, Giancarlo Franciò, Walter Leitner, Ruthenium-catalysed asymmetric hydrogenation of ketones using QUINAPHOS as the ligand Chemical Communications. ,vol. 2005, pp. 3460- 3462 ,(2005) , 10.1039/B505195A
Jeroen Wassenaar, Joost N. H. Reek, Hybrid bidentate phosphorus ligands in asymmetric catalysis: Privileged ligand approach vs. combinatorial strategies Organic and Biomolecular Chemistry. ,vol. 9, pp. 1704- 1713 ,(2011) , 10.1039/C0OB00732C
Lavinia Panella, Ben L. Feringa, Johannes G. de Vries, Adriaan J. Minnaard, Enantioselective RH-catalyzed hydrogenation of enol acetates and enol carbamates with monodentate phosphoramidites. Organic Letters. ,vol. 7, pp. 4177- 4180 ,(2005) , 10.1021/OL051559C
Takeshi Ohkuma, Christian A. Sandoval, Rajagopal Srinivasan, Quinghong Lin, Yinmao Wei, Kilian Muñiz, Ryoji Noyori, Asymmetric Hydrogenation oftert-Alkyl Ketones Journal of the American Chemical Society. ,vol. 127, pp. 8288- 8289 ,(2005) , 10.1021/JA052071+
Susanne Leuchs, Thomas Nonnen, Dominique Dechambre, Shukralla Na’amnieh, Lasse Greiner, Continuous biphasic enzymatic reduction of aliphatic ketones Journal of Molecular Catalysis B-enzymatic. ,vol. 88, pp. 52- 59 ,(2013) , 10.1016/J.MOLCATB.2012.09.017