Dataset Information

Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids.

ABSTRACT: For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in C-C bond-forming hydrogen-borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub-stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ-aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen-borrowing intermediate, removing the need for column chromatography.

SUBMITTER: Hall CJJ

PROVIDER: S-EPMC8048514 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids.

Hall Christopher J J CJJ Goundry William R F WRF Donohoe Timothy J TJ

Angewandte Chemie (International ed. in English) 20210224 13

For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in C-C bond-forming hydrogen-borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub-stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleav ...[more]

PMID: 33561302

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Project description:Construction of a C-C bond via alkylation of ketones with alcohol as the alkylating source by employing hydrogen-borrowing strategy is attracting significant attention and is highly appealing due to its simplicity, cost-effectiveness, environmental benefits, and the fact that water is the only byproduct. The development of heterogeneous catalysts based on nonprecious base metals is progressing rapidly. Our newly disclosed manganese-doped cerium oxide nanocomposite (10 wt % Mn@CeO2) stands out as a cost-efficient and air-stable catalyst, synthesized through a straightforward coprecipitation method and employed for α-alkylation of ketones with primary alcohols via the hydrogen-borrowing strategy. X-ray diffraction (XRD) analysis confirms the high crystallinity of CeO2, while field emission scanning electron microscopy (FE-SEM) and high-resolution transmission electron microscopy (HR-TEM) images reveal MnO2 nanoparticles, measuring 19 nm in size, uniformly decorated on the rod-shaped CeO2 nanoparticles, which have a size of 33 nm. X-ray photoelectron spectroscopy (XPS) analysis uncovers the presence of Mn4+ species embedded on the CeO2 nanorods. Electron paramagnetic resonance (EPR) analysis further indicates that surface defects contribute to the impressive catalytic yield, which ranges from 70 to 98% for the α-alkylated ketones. Thermogravimetric analysis (TGA) demonstrates the remarkable thermal stability of the catalyst, maintaining its stability up to 800 °C. Additionally, inductively coupled plasma mass spectrometry (ICP-MS) confirms no leaching of Mn ions, emphasizing the high heterogeneity of the catalyst. Remarkably, 10 wt % Mn@CeO2 nanocomposite is recycled for six cycles with no loss of catalytic activity. This study underscores the synergistic effect between the base metal MnO2 and redox pair of CeO2, which is key to the exceptional catalytic activity in α-alkylation reactions, making 10 wt % Mn@CeO2 a highly promising catalyst for sustainable and efficient C-C bond formation.

Dataset Information

Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids.

Publications

Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids.

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