Asymmetric Synthesis of Vabicaserin via Oxidative Multicomponent Annulation and Asymmetric Hydrogenation of a 3,4-Substituted Quinolinium Salt

2013 ◽  
Vol 15 (12) ◽  
pp. 2942-2945 ◽  
Author(s):  
Vladimir Dragan ◽  
J. Christopher McWilliams ◽  
Ross Miller ◽  
Karen Sutherland ◽  
John L. Dillon ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Hydrogenation ◽  
Quinolinium Salt

ChemInform Abstract: Convenient General Asymmetric Synthesis of Roche Ester Derivatives Through Catalytic Asymmetric Hydrogenation: Steric and Electronic Effects of Ligands.

ChemInform ◽  
2009 ◽  
Vol 40 (11) ◽  
Author(s):  
Cyrielle Pautigny ◽  
Severine Jeulin ◽  
Tahar Ayad ◽  
Zhaoguo Zhang ◽  
Jean-Pierre Genet ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Hydrogenation ◽  
Electronic Effects ◽  
Catalytic Asymmetric ◽  
Catalytic Asymmetric Hydrogenation

The Stereochemistry of Organometallic Compounds. XXIX. Synthesis of Steroidal 1,4-Diphosphine, 1,3-Diphosphine and 1,6-Diphosphine and Their Evaluation as Ligands in Metal Catalyzed Asymmetric Synthesis

1987 ◽  
Vol 40 (6) ◽  
pp. 1083 ◽  
Author(s):  
RJ Thomson ◽  
WR Jackson ◽  
D Haarburger ◽  
EI Klabunovsky ◽  
VA Pavlov
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Hydrogenation ◽  
Organometallic Compounds ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Hydrogenation Reactions ◽  
Metal Catalyzed ◽  
Asymmetric Carbon

The steroidal 1,4-diphosphines 3α- and 3β-diphenylphosphino-2a-(2'-diphenylphosphinoethyl)-5α-cholestanes and their 5H-benzo[b] phosphindole derivatives have been prepared and shown to be useful ligands in asymmetric hydrogenation reactions. Interestingly the 3α- and 3β-derivatives lead to opposing enantioselection preferences when used in these reactions. A steroidal 1,3-diphosphine, 3α-diphenylphosphino-2α-diphenylphosphinomethyl-5α-cholestane, has been prepared as a mixture containing some of the 3β-epimer. The 3α-1,3-diphosphine led to similar enantioselection in hydrogenation reactions as the 3α-1,4-diphosphine, and a model is proposed to explain the sense of the enantioselectivity in the 1,4- and 1,3-diphosphines. A steroidal 1,6-diphosphine has also been prepared but leads to lower optical yields in the hydrogenation reactions. These ligands have been shown to lead to only poor to moderate optical yields when used in asymmetric carbon-carbon bond forming reactions.

Asymmetric Synthesis of Chiral δ-lactones using BINAP-ruthenium(II) Complexes Hydrogenation Catalysts

2002 ◽  
Vol 2002 (11) ◽  
pp. 567-569 ◽  
Author(s):  
Yanjun Li ◽  
Taeko Izumi
Keyword(s):  
Asymmetric Synthesis ◽  
Ruthenium Complexes ◽  
Asymmetric Hydrogenation ◽  
Optical Purity ◽  
Hydrogenation Catalysts ◽  
Keto Acids ◽  
Chiralcel Od ◽  
High Yields

Asymmetric hydrogenation of keto-acids was accomplished by catalytic amounts of BINAP-ruthenium complexes to afford the corresponding δ-lactones in high yields. The optical purity of the synthesised δ-lactones was determined by chiralcel (OD) in the 9–56% range.

Asymmetric hydrogenation via architectural and functional molecular engineering

2001 ◽  
Vol 73 (2) ◽  
pp. 227-232 ◽  
Author(s):  
Ryoji Noyori ◽  
Masatoshi Koizumi ◽  
Dai Ishii ◽  
Takeshi Ohkuma
Keyword(s):  
Asymmetric Synthesis ◽  
Nitro Group ◽  
Functional Group ◽  
Asymmetric Hydrogenation ◽  
Molecular Engineering ◽  
The Novel ◽  
Bifunctional Mechanism ◽  
Chiral Compounds ◽  
Halogen Atoms ◽  
Metal Ligand

RuCl2 (phosphine) 2 (1,2-diamine) complexes, coupled with an alkaline base in 2-propanol, allows for preferential hydrogenation of a C=O function over coexisting conjugated or nonconjugated C=C linkages, a nitro group, halogen atoms, and various heterocycles. The functional group selectivity is based on the novel metal-ligand bifunctional mechanism. The use of appropriate chiral diphosphines and diamines results in rapid and productive asymmetric hydrogenation of a range of aromatic, hetero-aromatic, and olefinic ketones. The versatility of this method is manifested by the asymmetric synthesis of various biologically significant chiral compounds.

ChemInform Abstract: Asymmetric Hydrogenation of 3,5-Dioxoesters Catalyzed by the Ru/BINAP Complex: A Short Step Asymmetric Synthesis of 6-Substituted 5,6- Dihydro-2-pyrones.

ChemInform ◽  
2010 ◽  
Vol 24 (26) ◽  
pp. no-no
Author(s):  
L. SHAO ◽  
H. KAWANO ◽  
M. SABURI ◽  
Y. UCHIDA
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Hydrogenation

Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin via iridium-catalyzed asymmetric hydrogenation

2021 ◽  
Vol 57 (2) ◽  
pp. 195-198
Author(s):  
Xiang-Yu Ye ◽  
Zhi-Qin Liang ◽  
Cong Jin ◽  
Qi-Wei Lang ◽  
Gen-Qiang Chen ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Asymmetric Hydrogenation ◽  
High Reactivity ◽  
Iridium Complexes ◽  
Oxazoline Ligands

A series of highly rigid oxa-spiro phosphine–oxazoline ligands (O-SIPHOX) were synthesized efficiently, their iridium complexes showed high reactivity and enantioselectivity in the synthesis of key intermediate of anti-obesity drug lorcaserin.

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