1104662-19-2Relevant academic research and scientific papers
Iridium-catalyzed asymmetric hydrogenation of β-ketophosphonates with chiral ferrocenyl P,N,N-ligands
Ma, Yin-Feng,Hou, Chuan-Jin,Wei, De-Quan,He, Xinwei,Chu, Ting-Ting,Chen, Xiu-shuai,Hu, Xiang-Ping
, (2021/05/03)
The asymmetric hydrogenation of β-ketophosphonates with chiral Ir/P,N,N-ligands catalyst has been developed. A series of β-ketophosphonates were hydrogenated, and the corresponding β-hydroxyphosphonates were obtained in high yields with good or excellent
Highly enantioselective hydrogenation of β-acyloxy and β-acylamino α,β-unsaturated phosphonates catalyzed by rhodium phosphane-phosphite complexes
Chavez, M. Angeles,Vargas, Sergio,Suarez, Andres,Ulvarez, Eleuterio,Pizzano, Antonio
experimental part, p. 2775 - 2794 (2011/12/21)
The enantioselective hydrogenation of β-(acyloxy)- and β-(acylamino)vinylphosphonates with rhodium catalysts based on chiral phosphane-phosphite ligands has been studied. In the case of the β-(acyloxy)vinylphosphonates, the reaction also produces an achiral phosphonate resulting from the elimination of the benzoate group. High ligand modularity has led to a highly chemo- and enantioselective catalyst for both types of substrates, which afford a good range of β-acyloxy- and β-acylaminophosphonates with enantioselectivities between 90 and 99% ee. Most interestingly, the configuration of the hydrogenation products indicates the same stereochemical sense for the reduction of both types of substrates, which is opposite to that observed before for α-(acyloxy) vinylphosphonates. This observation has been rationalized by assuming the formation of a β-alkyl intermediate during the catalytic cycle, which also explains the formation of the elimination product in the hydrogenation of the β-(acyloxy)-vinylphosphonates. Copyright
Nonenzymatic kinetic resolution of racemic β-hydroxyalkanephosphonates with a chiral copper catalyst
Moriyama, Atsushi,Matsumura, Shintaro,Kuriyama, Masami,Onomura, Osamu
experimental part, p. 810 - 824 (2010/11/04)
Kinetic resolution of β-hydroxyalkanephosphonates was efficiently performed by 2-fluorobenzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with good s value of up to 21.
Highly enantioselective hydrogenation of enol ester phosphonates: A versatile procedure for the preparation of chiral β-hydroxyphosphonates
Vargas, Sergio,Suarez, Andres,Alvarez, Eleuterio,Pizzano, Antonio
supporting information; experimental part, p. 9856 - 9859 (2009/10/02)
A study was conducted to demonstrate a procedure for the preparation of chiral β-hydroxyphosphonates. The reaction sequence was investigated and the validity of the approach was demonstrated. The study also reported an olefin hydrogenation reaction, which gives access to a wide variety of chiral β-hydroxyphosphonates 2, with excellent levels of asymmetric induction, which can be converted into the corresponding alcohols. The application of phosphane-phosphite ligands 4 and 5 were investigated in diverse hydrogenation reactions. Unsaturated phosphonates 1 were chosen as substrates, in an effort to broaden the scope of these catalysts. Investigations were also initiated by the development of a convenient procedure for the synthesis of a set of olefins 1.
