Organocatalytic Asymmetric Mannich Reaction of Aromatic Imines

2025 · doi:10.3762/bxiv.2025.57.v1
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Amino acid-derived organocatalysts enabled asymmetric Mannich reactions of aromatic imines with malonates, achieving up to 98% enantiomeric purity through hydrogen/halogen bonding and steric effects.

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The paper studied asymmetric organocatalysis by synthesizing and screening multifunctional enantiomerically pure organocatalysts for an asymmetric Mannich reaction of aromatic imines with malonates. Using amino acid–derived catalysts, the authors report Mannich adducts formed with very high enantiomeric purities, reaching up to 98% ee, and propose that a network of hydrogen and halogen bonding to Lewis bases plus the steric effect of a tert-butyl group accounts for the stereoselectivity. The work is presented as a chemical methods/preprint with no explicit limitations stated in the provided text. The paper does not explicitly discuss endometriosis or adenomyosis; it was included in the corpus via a keyword match in the upstream search index.

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Abstract

Various multifunctional enantiomerically pure organocatalysts were synthesized and screened in asymmetric Mannich reaction. Aromatic imines gave Mannich adducts with malonates in the presence of amino acid derived catalyst in very high enantiomeric purities (ee up to 98%). It is proposed that the network of hydrogen and halogen bonds with Lewis bases, together with the steric effect of the tert -butyl group of the catalyst, is responsible for the high stereoselectivity of the reaction.
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Materials

chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry Various multifunctional enantiomerically pure organocatalysts were synthesized and screened in asymmetric Mannich reaction. Aromatic imines gave Mannich adducts with malonates in the presence of amino acid derived catalyst in very high enantiomeric purities (ee up to 98%). It is proposed that the network of hydrogen and halogen bonds with Lewis bases, together with the steric effect of the tert-butyl group of the catalyst, is responsible for the high stereoselectivity of the reaction.

Keywords

aromatic imine; asymmetric catalysis; Mannich reaction; non-covalent interactions; organocatalysis | Format: PDF | Size: 4.6 MB | Download | When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information: Kriis, K.; Martõnov, H.; Miller, A.; Peterson, M.; Järving, I.; Kanger, T. Beilstein Arch. 2025, 202557. doi:10.3762/bxiv.2025.57.v1 Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below. Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero. © 2025 Kriis et al.; licensee Beilstein-Institut. This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.

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