26919-86-8Relevant academic research and scientific papers
Practical enantioselective hydrogenation of α-aryl- and α-carboxyamidoethylenes by rhodium(I)-{1,2-bis[(o-tert-butoxyphenyl) (phenyl)phosphino]ethane}
Mohar, Barbara,Stephan, Michel
, p. 594 - 600 (2013/05/09)
The rhodium(I)-{1,2-bis[(o-tert-butoxyphenyl)(phenyl)phosphino]ethane} [Rh(I)-(t-Bu-SMS-Phos)] catalyst system displayed prime efficiency in the hydrogenation of large series of aamidostyrenes and a-amidoacrylates. Up to >99.9% enantiomeric excesses coupl
Air-stable P-chiral bidentate phosphine ligand with (1-adamantyl) methylphosphino group
Imamoto, Tsuneo,Kumada, Atsushi,Yoshida, Kazuhiro
, p. 500 - 501 (2008/02/10)
Air-stable diphosphine ligand, (R,R)-2,3-bis((1-adamantyl)-methylphosphino) quinoxaline, was prepared by the reaction of enantiomerically pure (S)-(1-adamantyl)methylphosphine-borane with 2,3-dichloroquinoxaline. The ligand exhibited excellent enantiosele
PROCESS FOR PRODUCING OPTICALLY ACTIVE DIMER OF PHOSPHORUS HETEROCYCLE
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Page/Page column 18, (2010/11/08)
Primary phosphine represented by formula (1): ????????[Chem. 1] R-PH2?????(1) (wherein R represents a linear, branched, or cyclic alkyl group having 2 to 20 carbon atoms) is reacted with a compound represented by formula (2): ????????[Chem. 2]
PipPhos and MorfPhos: Privileged monodentate phosphoramidite ligands for rhodium-catalyzed asymmetric hydrogenation
Bernsmann, Heiko,Van Den Berg, Michel,Hoen, Rob,Minnaard, Adriaan J.,Mehler, Gerlinde,Reetz, Manfred T.,De Vries, Johannes G.,Feringa, Ben L.
, p. 943 - 951 (2007/10/03)
(Chemical Equation Presented) A library of 20 monodentate phosphoramidite ligands has been prepared and applied in rhodium-catalyzed asymmetric hydrogenation. This resulted in the identification of two ligands, PipPhos and MorfPhos, that afford excellent
Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximes.
Cooper, Tracey S,Laurent, Pierre,Moody, Christopher J,Takle, Andrew K
, p. 265 - 276 (2007/10/03)
A new asymmetric synthesis of alpha-amino acids is described in which the key step is the highly diastereoselective addition of organolithium carboxyl synthons (2-furyllithium, phenyllithium, vinyllithium) to (R)- and (S)-O-(1-phenylbutyl) oximes to give hydroxylamines, with vinyllithium being the most satisfactory nucleophilic reagent. Subsequent reductive cleavage of the N-O bond in hydroxylamines, followed by N-protection, and oxidative cleavage of the carboxyl precursor gave a range of N-protected amino acids and esters. The method was exemplified by the synthesis of a range of derivatives of non-proteinogenic amino acids such as 4-bromophenylalanine, tert-leucine, norvaline, cyclohexyl- and aryl-glycines, 2-amino-8-oxodecanoic acid (Aoda) and alpha-methylvaline.
Kinetic resolution of amines: A highly enantioselective and chemoselective acetylating agent with a unique solvent-induced reversal of stereoselectivity
Arseniyadis, Stellios,Valleix, Alain,Wagner, Alain,Mioskowski, Charles
, p. 3314 - 3317 (2007/10/03)
Solvents lend a hand: Changing the polarity of the reaction solvent from 1,3-dimethyltetrahydropyrimidin-2-one (DMPU) to toluene reverses the stereo-selectivity observed in the acetylation of amines with (1S,2S)-1 (see scheme). Optimizing the reaction conditions led to an unprecedented 90% ee (S) in DMPU at -20°C with a 33% conversion.
Optically active 1,1′-Di-tert-butyl-2,2′-diphosphetanyl and its application in rhodium-catalyzed asymmetric hydrogenations
Imamoto, Tsuneo,Oohara, Nobuhiko,Takahashi, Hidetoshi
, p. 1353 - 1358 (2007/10/03)
(1S,1′S,2R,2′R)-1, 1′-Di-tert-butyl-2,2′- diphosphetanyl was prepared from fert-butylphosphine via phosphine-boranes as intermediates. The rhodium complex of the ligand was used as a highly efficient catalyst in asymmetric hydrogenations of α-acetyl-amino
Asymmetric hydrogenation of enamides with Rh-BisP* and Rh-MiniPHOs catalysts. Scope, limitations, and mechanism
Gridnev,Yasutake,Higashi,Imamoto
, p. 5268 - 5276 (2007/10/03)
The asymmetric hydrogenation of aryl- and alkyl-substituted enamides catalyzed by Rh-BisP* complex affords optically active amides with very high ee values. The Rh-MiniPHOS catalyst gives somewhat less satisfactory results. Hydrogenation of the aryl-subst
Diastereoselective addition of chiral aliphatic imines and 2-alkyl-1,3-oxazolidines to organometallic reagents
Higashiyama,Fujikura,Takahashi
, p. 722 - 728 (2007/10/02)
The reaction of organocerium reagents with chiral aliphatic imines derived from (R)-O-methylphenylglycinol afforded the corresponding amines with high diastereoselectivity. In contrast, the reaction of Grignard reagents with chiral 2-alkyl-1,3-oxazolidines derived from (R)-N-methylphenylglycinol afforded the amines with changeover in diastereoselectivity.
Chromatographic Resolutions of Racemates, XI. Comparison of Optically Active Polyamides and Cellulose Triacetate
Blaschke, Gottfried,Kraft, Horst Peter,Markgraf, Hildegunde
, p. 3611 - 3617 (2007/10/02)
On optically active polyacrylic and polymethacrylic amides (1a-e) as well as on microcrystalline cellulose triacetate (2), numerous racemates including drugs are separated at least partially, the amide 4f completely on cellulose triacetate.By repeated chromatography on the polyamide 1a, (+)- and (-)-mandelic acid (4a) and (+)-hexobarbital (9d) also were obtained optically pure.
