592503-41-8Relevant academic research and scientific papers
Highly enantioselective asymmetric hydrogenation of β-acetamido dehydroamino acid derivatives using a three-hindered quadrant rhodium catalyst
Wu, He-Ping,Hoge, Garrett
, p. 3645 - 3647 (2004)
(Chemical Equation Presented) A previously reported three-hindered quadrant chiral ligand and its corresponding rhodium complex provide high enantioselectivity for the asymmetric hydrogenation of β-acetamido dehydroamino acid substrates. Both (E)- and (Z)-substrates are hydrogenated with high enantioselectivity in all of the reported examples. Asymmetric hydrogenation of a cyclic β-acetamido dehydroamino acid substrate in 85% ee is also reported.
Development of a suitable process for the preparation of a TNF-α converting enzyme inhibitor, WAY-281418
Wang, Youchu,Papamichelakis, Maria,Chew, Warren,Sellstedt, John,Noureldin, Razzak,Tadayon, Sam,Daigneault, Sylvain,Galante, Rocco J.,Sun, Jerry
, p. 1253 - 1260 (2013/01/03)
A suitable process for the preparation of kilogram quantities of a TNF-α converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydroge-nation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.
C1-symmetric bisphosphine ligands and their use in the asymmetric synthesis of pregabalin
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Page/Page column 22-23, (2008/06/13)
Materials and methods for preparing (S)-(+)-3-(aminomethyl)-5-methyl-hexanoic acid and structurally related compounds via enantioselective hydrogenation of prochiral olefins are disclosed. The methods employ novel chiral catalysts, which include C1-symmetric bisphosphine ligands bound to transition metals.
Preparation of chiral cyclic amino acids and derivatives
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Page 4, (2010/02/09)
Cyclic β-(acylamino)acrylate derivatives were hydrogenated using Ru-chiral phosphine ligand catalysts and thereafter converted to the corresponding cyclic β-aminoacids in high yield and enantioselectivity according to the reaction scheme:
Enantioselective hydrogenation of tetrasubstituted olefins of cyclic β-(acylamino)acrylates
Tang, Wenjun,Wu, Shulin,Zhang, Xumu
, p. 9570 - 9571 (2007/10/03)
Hydrogenation of a series of cyclic β-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an efficient catalytic method for the synthesis of both cis and trans chiral cyclic β-amino acid derivatives. Copyright
