Rare Gold-Catalyzed 4-<i>exo</i>-<i>dig</i> Cyclization for Ring Expansion of Propargylic Aziridines toward Stereoselective (<i>Z</i>)-Alkylidene Azetidines, via Diborylalkyl Homopropargyl Amines
We report an uncommon 4-<i>exo</i>-<i>dig</i> cyclization of <i>N</i>-tosyl homopropargyl amines, catalyzed by [AuCl(PEt<sub>3</sub>)]/AgOTf, to prepare stereoselective (<i>Z</i>)-2-alkylidene-1-tosylazetidine compounds. The reaction outcome contrasts with the gold-catalyzed cyclization of <i>N</i>-tosyl homopropargyl amines containing a methyl group at the propargylic position that provides substituted 2,3-dihydropyrroles via a 5-<i>endo</i>-<i>dig</i> mechanism. The access to <i>N</i>-tosyl homopropargyl amines is possible by the regioselective nucleophilic attack of α-diboryl alkylidene lithium salts to propargylic aziridines.
Authors
- M. Mar Díaz‐Requejo (ORCID: https://orcid.org/0000-0001-8295-4059)
- Pedro J. Pérez (ORCID: https://orcid.org/0000-0002-6899-4641)
- Oriol Salvadó (ORCID: https://orcid.org/0000-0002-3493-8211)
- Elena Fernández (ORCID: https://orcid.org/0000-0001-9025-1791)
- Jorge Pérez‐Ruíz (ORCID: https://orcid.org/0009-0000-2649-4801)
- Alba Mesas
Institutions
- Universitat Rovira i Virgili (ES)
- Universidad de Huelva (ES)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-02
- DOI
- https://doi.org/10.1021/acs.orglett.4c02415
- Citations
- 9
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.25
Funders
- Ministerio de Ciencia e Innovación
- European Regional Development Fund