Induktion von Asymmetrie durch Aminosäuren

Drauz, Karlheinz; Kleemann, Axel; Martens, Jürgen

doi:10.1002/ange.19820940804

Cited by 76 publications

(1 citation statement)

References 280 publications

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“…The asymmetric hydrogenation of dehydropeptides with rhodium(I) complexes of optically active diphosphines as catalysts was often studied and high diastereomeric excess was achieved (Scheme , Equation (40)) 289–293. The interactions of the two chiral centers (one at the phosphino ligand, the other in the dehydropeptide) can lead to a reduced or enhanced stereoselectivity 293. The mechanism includes a hydrido‐olefin‐rhodium(III) complex and a rhodium–carbon‐σ‐bond as intermediates 294…”

Section: Modification Of Peptides By Use Of Metal Catalysts or Mementioning

confidence: 99%

Metal Complexes of Biologically Important Ligands, CLXXVI.[1] Formation of Peptides within the Coordination Sphere of Metal Ions and of Classical and Organometallic Complexes and Some Aspects of Prebiotic Chemistry

Beck

2011

Zeitschrift anorg allge chemie

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Section: Modification Of Peptides By Use Of Metal Catalysts or Mementioning

confidence: 99%

Metal Complexes of Biologically Important Ligands, CLXXVI.[1] Formation of Peptides within the Coordination Sphere of Metal Ions and of Classical and Organometallic Complexes and Some Aspects of Prebiotic Chemistry

Beck

2011

Zeitschrift anorg allge chemie

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New Chiral Catalysts ContainingN,O-Heterocycles Derived from Chiral Amino Alcohols

Juanes

Rodríguez‐Ubis

Brunet³

et al. 1999

Eur. J. Org. Chem.

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The enantioselectivity exerted by a new series of chiral catalysts containing N,O‐heterocycles of different sizes has been checked in the addition of diethylzinc to benzaldehyde, which was used as a model reaction. The catalysts were derived from natural amino acids, following a relatively simple procedure, and in several cases excellent ee values were obtained. The results were complementary since ee's ranged from 98% (R) to 94% (S) excesses of the final 1‐phenylpropan‐1‐ol. Molecular mechanics calculations suggested that the production of the R alcohol may be explained by a mechanism similar to that described by Noyori, in which ZnEt2 interacts solely with the N–C–C–OH fragment, whereas the formation of the S enantiomer needed the direct participation of the lateral chain of the parent amino acid and the N,O‐heterocycle.

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Biometallorganische Chemie – Übergangsmetallkomplexe mit α-Aminosäuren und Peptiden

Severin¹,

Bergs²,

Beck³

1998

Angewandte Chemie

105

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Ein neues interdisziplinäres Forschungsgebiet ist die Biometallorganische Chemie; sie befaßt sich mit der Einführung von metallorganischen Fragmenten in Biomoleküle (siehe z. B. Struktur rechts). Die „klassischen”︁ α‐Aminosäure‐ und Peptidliganden haben sich dabei als besonders vielseitig erwiesen und eröffnen unter anderem einen Zugang zu stereochemisch interessanten Verbindungen. α‐Aminosäuren und Peptide können durch metallorganische Verbindungen synthetisiert, markiert, stabilisiert oder aktiviert werden.

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Induktion von Asymmetrie durch Aminosäuren

Cited by 76 publications

References 280 publications

Metal Complexes of Biologically Important Ligands, CLXXVI.[1] Formation of Peptides within the Coordination Sphere of Metal Ions and of Classical and Organometallic Complexes and Some Aspects of Prebiotic Chemistry

Metal Complexes of Biologically Important Ligands, CLXXVI.[1] Formation of Peptides within the Coordination Sphere of Metal Ions and of Classical and Organometallic Complexes and Some Aspects of Prebiotic Chemistry

New Chiral Catalysts ContainingN,O-Heterocycles Derived from Chiral Amino Alcohols

Biometallorganische Chemie – Übergangsmetallkomplexe mit α-Aminosäuren und Peptiden

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