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Literature DB >> 27763714

Bifunctional Ammonium Salt Catalyzed Asymmetric α-Hydroxylation of β-Ketoesters by Simultaneous Resolution of Oxaziridines.

Johanna Novacek¹, Joseph A Izzo², Mathew J Vetticatt², Mario Waser¹.

Abstract

Chiral bifunctional urea-containing ammonium salts were found to be very efficient catalysts for asymmetric α-hydroxylation reactions of β-ketoesters with oxaziridines under base-free conditions. The reaction is accompanied by a simultaneous kinetic resolution of the oxaziridine and a plausible and so far unprecedented bifunctional transition-state model has been obtained by means of DFT calculations.

Entities: Chemical

Keywords: asymmetric catalysis; ion pairs; non-covalent interactions; resolution; transition-state model

Year: 2016 PMID： 27763714 DOI： 10.1002/chem.201604153

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

10 in total

1. Quaternary β^2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides.

Authors: Andreas Eitzinger; Michael Winter; Johannes Schörgenhumer; Mario Waser
Journal: Chem Commun (Camb) Date: 2019-12-12 Impact factor: 6.222

2. Synthesis of α-CF₃-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

Authors: Michael Winter; Kirill Faust; Markus Himmelsbach; Mario Waser
Journal: Org Biomol Chem Date: 2019-06-12 Impact factor: 3.876

3. Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides.

Authors: Lingjun Xu; Shuwen Han; Linjie Yan; Haifeng Wang; Haihui Peng; Fener Chen
Journal: Beilstein J Org Chem Date: 2018-01-31 Impact factor: 2.883

4. Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy.

Authors: Guglielmo Monaco; Maximilian Tiffner; Antonia Di Mola; Wouter Herrebout; Mario Waser; Antonio Massa
Journal: Molecules Date: 2020-05-12 Impact factor: 4.411

Bifunctional Ammonium Salt Catalyzed Asymmetric α-Hydroxylation of β-Ketoesters by Simultaneous Resolution of Oxaziridines.

1. Quaternary β^2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides.

2. Synthesis of α-CF₃-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

3. Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides.

4. Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy.

5. Asymmetric phase-transfer catalysed β-addition of isoxazolidin-5-ones to MBH carbonates.

Review 6. Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

Review 7. Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines.

8. Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters.

9. Enantiospecific deoxyfluorination of cyclic α-OH-β-ketoesters.

10. Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with β-Keto Esters.