Preparation of furfural derived enantioenriched vinyl oxazoline building block and exploring its reactivity

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 N-Alloc protected furfuryl amino alcohols derived from furfural and L- or D-valinol were subjected to Torii-type ester electrosynthesis to obtain the corresponding unsaturated esters. These served as key intermediates to prepare enantioenriched (S)- and (R)- unsaturated amides by N-Alloc deprotection which induced concomitant methoxymethyl group cleavage, O- to N- rearrangement, and isomerization of the double bond. An oxazoline ring formation in the resulting unsaturated amides provided the corresponding enantioenriched vinyl oxazolines. The reactivity of the electron deficient double bond in the vinyl oxazoline was explored in several reactions. Out of these, aza-Diels-Alder with TsNCO was successful, leading to a highly diastereoselective formation of oxazolo[3,2-c]pyrimidine derivative.

furanoics; electrosynthesis; oxazoline; asymetric synthesis; aza-Diels-Alder | Format: DOCX | Size: 20.6 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: Darzina, M.; Lielpetere, A.; Jirgensons, A. Beilstein Arch. 2025, 202535. doi:10.3762/bxiv.2025.35.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 Darzina 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.