Stereoselektive Synthesen, II. Die stereoselektive Acylierung racemischer primärer Amine durch optisch aktive gemischte Anhydride

Herlinger, Heinz; Kleimann, H.; Ugi, Ivar

doi:10.1002/jlac.19677060105

Cited by 29 publications

(3 citation statements)

References 27 publications

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“…Step one: chromatographic data acquisition for rac-9a-e. (i) Cbz N-protection, (ii) HCO 2 H, H 2 O, (iii) metal hydride reduction Inspection of the literature provided several examples of the selective and non-racemizing catalytic hydrogenation of a phenyl group in phenylglycine, phenylalanine or phenethylamine and analogues using ruthenium on carbon or rhodium on Al 2 O 3 (Sato et al 1998;Herlinger et al 1967;Strotmann and Butenschön 2000;Nugent 2002;Minnaard et al 1999;Hayashi et al 1983). These methods when applied to the hydrogenation of 3d on Rh/Al 2 O 3 or Ru/C catalyst gave quantitatively 3e.…”

Section: Scheme 5 Tandem Oxidation and Reduction To Recycle The Unresmentioning

confidence: 98%

Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

Albalat¹,

Primazot²,

Wilhelm³

et al. 2011

Amino Acids

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The first successful resolution of rac-α-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of α-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected α-aminoaldehyde intermediates. A racemization method of optically enriched α-aminoacetals is exemplified to allow valorisation of both enantiomers.

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Section: Scheme 5 Tandem Oxidation and Reduction To Recycle The Unresmentioning

confidence: 98%

Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

Albalat¹,

Primazot²,

Wilhelm³

et al. 2011

Amino Acids

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“…Herlinger et al studied the acylation of various racemic amines and amino esters with the mixed anhydrides obtained in situ from optically active carboxylic acids and ethyl chloroformate. [54] Acylation was carried out with 10:1 aminemixed anhydride molar ratio in CH 2 In 1968-1981 there was several communications on the acylative KR of a variety of racemic amines using diastereoselective reagents, such as the derivatives of camphoric acid, [55] tartaric anhydrides, [56] (S)-2-phenylpropionic and (S)-2-phenylbutyric acids. [57] However, the stereochemical results of the KR were reported to be from modest to low.…”

Section: Acylative Kr Of Racemic Amines With Diastereoselective Agentsmentioning

confidence: 99%

Nonenzymatic Acylative Kinetic Resolution of Racemic Amines and Related Compounds

2011

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Acylative kinetic resolution of racemic amines occupies a highly important place among the methods for preparation of enantio enriched or pure amines. Nonenzymatic acylative kinetic resolution is usually carried out in the presence of chiral acyl‐transfer catalysts or under the action of chiral enantio‐ or diastereoselective resolving agents. Recently, this line of investigations has been rapidly developed and very interesting results of design and synthetic application of both new catalysts and chiral acylating agents have been obtained. This microreview summarizes the recent advances in this area.

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“…Completeness of the reaction was checked b y 31P NM R. The relative reaction rates kA: k B were com puted according to the following eq. [15]:…”

Section: 4-cl2mentioning

confidence: 99%

2-(4-Toluenesulphonyl)-3-aryloxaziridines as Oxidizing Reagents for P(III) Compounds

Klein

Ugi

1992

Zeitschrift Für Naturforschung B

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The preparation o f four 2-(4-toluenesulphonyl)-3-aryloxaziridines by oxidation o f the cor responding imines by peracids is described. The relative oxidation rates o f trimethyl phosphite by these oxaziridines are determined.Until recently, no generally applicable oxidizing reagents were known for P(III) compounds, al though P(III) com pounds are readily oxidized to form the corresponding P(V) compounds. In 1972, a kinetic study of the deoxygenation of 2-alkyl-3-aryloxaziridines by tributylphosphine was described [9], F or a long time, the oxidation of P(III) com pounds by oxaziridines seems to have been neglected, although there has been consider R,jP + rJX -n-rS -"*"?"? p' -so.- The intermediacy of a phosphorane derivative 3 (R' = OEt; R2=Ph; R 3='Pr) was observed by 31P N M R (Ö = 19.52 ppm, H 3P 0 4) when triethyl phos phite was oxidized by 2 (R 2, R 3 as above) in CDC13[ 11].Recently, the racemates o f diastereom er mix tures of P(III) com pounds were reacted with chiral oxaziridines, and stereoselective destruction [12] of one stereoisomer was observed [13].In the present com m unication we would like to report on the syntheses of 2-(4-toluenesulphonyl)-3-aryloxaziridines (9).These oxaziridines can be used as widely appli cable oxidizing reagents o f P(III) com pounds.

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Stereoselektive Synthesen, II. Die stereoselektive Acylierung racemischer primärer Amine durch optisch aktive gemischte Anhydride

Abstract: An 35 Beispielen wurde die Stereoselektivität der Acylierung überschüssiger racemischer primärer Amine durch gemischte Anhydride aus optisch aktiven Carbonsäuren und Äthylkohlensäure untersucht.

Cited by 29 publications

References 27 publications

Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes

Nonenzymatic Acylative Kinetic Resolution of Racemic Amines and Related Compounds

2-(4-Toluenesulphonyl)-3-aryloxaziridines as Oxidizing Reagents for P(III) Compounds

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