Asymmetric tritiation of N-acetyl dehydrophenylalanyl-(S) phenylalanine (methylester) catalyzed with a rhodium (+) diop complex

Levine‐Pinto, H.; Morgat, Jean‐Louis; Fromageot, P.; Meyer, Dominique; Poulin, Jean-Claude; Kagan, Henri B.

doi:10.1016/0040-4020(82)85053-9

Cited by 21 publications

(1 citation statement)

References 14 publications

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“…In this case the auxiliary was removed by reduction with NaBH 4 to give (R)-2-(4-nitrophenyl)-1-[3-14 C]propanol (99 converted the alcohol into the corresponding amine 100, which has been further transformed to [ 14 C]LY50108, a drug substance developed for the treatment of cognitive disorders 98 . 39 (Figure 11.42) was prepared through diastereoselective a-methylation of the sodium enolate of (4R,5S)-3-(4-i-butenylphenyl)acetyl-4methyl-5-phenyl-1,3-oxazolidin-2-one (114) and LiOH/H 2 O 2 mediated cleavage of the auxiliary. 39 (Figure 11.42) was prepared through diastereoselective a-methylation of the sodium enolate of (4R,5S)-3-(4-i-butenylphenyl)acetyl-4methyl-5-phenyl-1,3-oxazolidin-2-one (114) and LiOH/H 2 O 2 mediated cleavage of the auxiliary.…”

Section: A-alkylation Of Chiral Imide Enolatesmentioning

confidence: 99%

Preparation of Enantiomerically Pure Compounds Labeled with Isotopes of Hydrogen and Carbon

Voges¹,

Heys

Moenius

2009

Preparation of Compounds Labeled With Tritium and Carbon‐14

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Section: A-alkylation Of Chiral Imide Enolatesmentioning

confidence: 99%

Preparation of Enantiomerically Pure Compounds Labeled with Isotopes of Hydrogen and Carbon

Voges¹,

Heys

Moenius

2009

Preparation of Compounds Labeled With Tritium and Carbon‐14

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Synthesis of tritium labelled (R) and (S)-3-aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part I

Masjedizadeh¹,

Parnes²

1996

J Label Compd Radiopharm

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SUMMARY(R) and (S)-3-aminoquinuclidines-3H with the specific activity of 35 Ci/mmol were prepared. Reduction of enamide 2 with carrier free tritium gas over RhCODCl dimer, (2S, 3s) Chiraphos in methanol gave yacemk amide &. Hydrolysis followed by resolution of the enantiomers with (R)-methyl benzyl isocyanate gave (R) and (S)-3-aminoquinuclidine-3H 1Oc-S and lOc-q. The enantiopurity purity of both isomers was >99.5%.

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Asymmetric tritiation of N‐acetyl α‐β dehydrotryptophanamide

Pinto‐Alphandary¹,

Craeynest‐Jimonet²,

Morgat³

et al. 1988

Labelled Comp Radiopharmac

Self Cite

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Present address : Unite d e s Agents Antibacteriens, CNRS U.A. 2 7 1 , I n s t i t u t Pasteur, 75724 Paris Cddex 15 (France). SmaUILI Rhodium-DiPAHP complex c a t a l y z e s the s t e r e o s e l e c t i v e a d d i t i o n of two tritium atoms on N-acetyl -a-B dehydrotryptophanamide. The s u b s t r a t e was prepared by dehydrogenation of N-acetyltryptophanamide with TSO (Tryptophan-Side Chain oxidase) from Pseudomonas. T r i t i a t e d N-acetyl-tryptophanamide was obtained with the t h e o r e t i c a l s p e c i f i c r a d i o a c t i v i t y ( 5 8 Ci/mmole). The enantiomeric exc e s s of the L-diasteroisomer reached 9 4 . 4 %. 3H NHR s p e c t r a indicated the select i v i t y of 3H-labelling on the C,-Cg double bond. This new approach of t r i t i a t i o n by homogeneous c a t a l y s i s applied to tryptophanyl-containing peptides is discussed.Key words : asymmetrict r i t i a t i o ntryptophandehydrogenase -TSO.

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Asymmetric tritiation of N-acetyl dehydrophenylalanyl-(S) phenylalanine (methylester) catalyzed with a rhodium (+) diop complex

Cited by 21 publications

References 14 publications

Preparation of Enantiomerically Pure Compounds Labeled with Isotopes of Hydrogen and Carbon

Preparation of Enantiomerically Pure Compounds Labeled with Isotopes of Hydrogen and Carbon

Synthesis of tritium labelled (R) and (S)-3-aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part I

Asymmetric tritiation of N‐acetyl α‐β dehydrotryptophanamide

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