Optisch aktive N-phosphinomethylierte α-aminosäuren: synthese und anwendung als liganden in asymmetrischen hydrierungen mit rhodium-komplexen

Kellner, K.; Tzschach, A.; Nagy-Magos, Zsuzsa; Marko, L.

doi:10.1016/s0022-328x(00)90290-0

Cited by 35 publications

(12 citation statements)

References 4 publications

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“…The relatively mild reaction conditions, the large number of substructures available, and the lack of a protection/ deprotection step for the phosphine functional group made this one-step synthesis of phosphines an attractive target for parallel synthesis. Aminomethylphosphines have been used as supporting ligands for a variety of hydrogenation 20,21 and hydroformylation 19,21 catalysts. We were interested in expanding the scope of the aminomethylphosphine synthesis to include aldehydes other than formaldehyde and avoiding the use of protic solvents, elevated temperatures, and extensive purification procedures.…”

Section: Resultsmentioning

confidence: 99%

Parallel Synthesis of Aminomethylphosphine Ligands

LaPointe¹

1998

J. Comb. Chem.

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Section: Resultsmentioning

confidence: 99%

Parallel Synthesis of Aminomethylphosphine Ligands

LaPointe¹

1998

J. Comb. Chem.

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“…[NEt 4 ] 2 [Re(CO) 3 Br 3 ] was prepared by the published procedure [9] . 1 [10] with only slight modifications. 31 1953, 1945, 1925, 1907 (CO).…”

Section: Methodsmentioning

confidence: 99%

“…Bis(diphenylphosphinomethyl)amines are good candidates for the pre-formed chelate approach. They are readily synthesised via the Mannich reaction between primary amines and secondary phosphines (with formaldehyde) [10] or bis(hydroxymethyl)phosphonium salts [15] , and are known to form stable chelate complexes with palladium, platinum and rhodium [16] . In principle, any desired functional group (for protein conjugation or for increasing water-solubility) can be attached onto the nitrogen atom by appropriate choice of the NH 2 group-containing starting material (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Tricarbonylrhenium(I) complexes of phosphine-derivatized amines, amino acids and a model peptide: structures, solution behavior and cytotoxicity

Zhang

Vittal

Henderson

et al. 2002

Journal of Organometallic Chemistry

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Modified Mannich reactions of amines, amino acids and a model peptide with Ph 2 PH and CH 2 O gave bis(diphenylphosphinomethyl)amines (Ph 2 PCH 2) 2 NR [R= Ph (1), CH 2 CH 2 OH (2), CH 2 COOCH 2 Ph (3), CH 2 CONHCH 2 COOCH 2 Ph (4), CH 2 COOH (5)] and (Ph 2 PCH 2) 2 NCH 2 CH 2 N(CH 2 PPh 2) 2 (6). Reaction with [ReBr 3 (CO) 3 ] 2under mild conditions led to ReBr(CO) 3 {(Ph 2 PCH 2) 2 NR} [R= Ph (7), CH 2 CH 2 OH (8), CH 2 COOCH 2 Ph (9), CH 2 CONHCH 2 COOCH 2 Ph (10), CH 2 COOH (11)] and [ReBr(CO) 3 Ph 2 PCH 2) 2 NCH 2 ] 2 (12). All new complexes have been characterized by NMR and IR spectroscopy and for 7, 9 and 10, single-crystal X-ray diffraction analyses. Stability studies by Electrospray Mass Spectrometry, showed that other than solvolysis, the complexes are fairly stable in neutral and acidic methanol. Cytotoxicity testing of 7-10 and 12 showed that all the complexes are active against specific tumour cell lines.

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“…Another interesting ligand exhibiting a mixed P/N donor set is Ph 2 PCH 2 N(Me)CH 2 PPh 2 which was first prepared in 1980 and has been investigated intensively over the years. [86][87][88][89][90][91][92] In 2008 our group synthesised the new PNP ligands N,N-bis(diphenylphosphinomethyl)-2-aminopyridine (pyNP 2 ) and N,N,N 0 ,N 0 -tetrakis(diphenylphosphinomethyl)-2,6-diaminopyridine (pyN 2 P 4 ) where the amino groups were supposed to act as a proton relay. 93 A dinitrogen complex could only be obtained with the ligand pyNP 2 where the pyridine moiety did not coordinate.…”

Section: Molybdenum and Tungsten N 2 Complexes With Mixed P/n Ligandsmentioning

confidence: 99%