Doyle, M. P. and Timmons, D. J. and Arndt, M. M. R. and Duursma, A. and Colyer, J. T. and Brunner, Henri (2001) First attempts at differential diastereoselection in catalytic reactions of N-chirally substituted dirhodium(II) tetrakis[methyl 2-oxoimidazolidine-4(S)-carboxylates] with diazoacetates. RUSSIAN CHEMICAL BULLETIN, 50 (11). pp. 2156-2161. ISSN 1066-5285
Full text not available from this repository. (Request a copy)Abstract
Chiral attachments on 2-oxoimidazolidine-4(S)-carboxylate ligands for dirhodium(11) can provide differential diastereoselection in catalytic reactions of diazo compounds. The synthesis of these heterocyclic ligands from the readily available amino acid asparagine is reported. Reactions with diazoacetates offering intramolecular carbon-hydrogen insertion provide evaluative data that demonstrate differential diastereoselection. Surprisingly, placement of a carbonyl group within the chiral attachment remove, enantiocontrol from the catalyst, presumably because of intramolecular ylide formation.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | METAL CARBENE TRANSFORMATIONS; HYDROGEN INSERTION REACTIONS; ENANTIOCONTROL; DIASTEREOCONTROL; chiral dirhodium(II) catalysts; catalysis; N-acylimidazolidinone-carboxylates.; asymmetric carbon-hydrogen insertion; metal carbene reactions |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 01 Dec 2021 14:17 |
| Last Modified: | 01 Dec 2021 14:17 |
| URI: | https://pred.uni-regensburg.de/id/eprint/41008 |
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