2026-06-27T23:06:08Zhttps://docta.ucm.es/rest/oai/request
oai:docta.ucm.es:20.500.14352/973002025-03-18T13:35:54Zcom_20.500.14352_14col_20.500.14352_15
Docta Complutense author Concellón, José M. author Bernad, Pablo L. author Suárez Álvarez, José Ramón author García-Granda, Santiago author Díaz, M. Rosario 2024-01-31T15:50:22Z 2024-01-31T15:50:22Z 2005 0022-3263 10.1021/jo0515069 https://hdl.handle.net/20.500.14352/97300 1520-6904 https://doi.org/10.1021/jo0515069 https://pubs.acs.org/doi/10.1021/jo0515069 The reaction of chiral 2-(1-aminoalkyl)aziridines with different thiols, in the presence of BF3‚Et2O, is reported. The obtained products were dependent on the structure of the starting aminoaziridines. Thus, enantiopure (2S,3S)-2-(alkylthio)alkane-1,3-diamines were obtained fromaziridines with C-2 substituents with lower steric congestion and partially racemized (2S,3S)-2,3-bis(alkylthio)alkan-1-amines3(ee)56-66%) from aziridines with larger C-2 subtituents. In both cases, the opening of the nonactivated aziridine ring at C-2 took place with retention of configuration and proceeded with regio- and stereoselectivity at C-2. In the synthesis of 3, 2 equiv of thiol reacts with and the opening of aziridine ring at C-2 was followed by an unusual displacement of the dibenzyl amino group by a second equivalent of thiol. The regio-chemistry and relative configuration of compounds was established by single-crystal X-ray analysis. A mechanism is proposed to explain the results obtained eng Selective Ring-Opening of Nonactivated Amino Aziridines by Thiols and Unusual Nucleophilic Substitution of a Dibenzylamino Group journal article 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URL https://docta.ucm.es/bitstreams/190f60dd-0e80-4a1b-80c4-a9d8f6e63437/download File MD5 7ac207f1977c0889bb5e91c804d8e0c9 126721 application/pdf Nonactivated_amino_aziridines.pdf URL https://docta.ucm.es/bitstreams/0ae01595-76be-4623-8b81-efcdef7c0c7f/download File MD5 98bcb145f0c55bcc50f4c0a37576e44d 33908 text/plain Nonactivated_amino_aziridines.pdf.txt