Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols
A change in mechanism was observed in the hypervalent iodine-mediated cyclization of <i>N</i>-alkenylamides when the carbon chain between the alkene and the amide increased from two to three atoms. In the latter case, cyclization at the amide nitrogen to form the pyrrolidine ring was favored over cyclization at the amide oxygen. A DFT study was undertaken to rationalize the change in mechanism of this cyclization process. In addition, reaction conditions were developed, and the scope of this cyclization studied.
Authors
- Jean‐Marc Sotiropoulos (ORCID: https://orcid.org/0000-0001-9513-3639)
- Konrad Kepski
- Wesley J. Moran (ORCID: https://orcid.org/0000-0002-5768-3629)
- Smaher E. Butt
Institutions
- Centre National de la Recherche Scientifique (FR)
- University of Huddersfield (GB)
- Université de Pau et des Pays de l'Adour (FR)
- Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux (FR)
- Keele University (GB)
Publication Details
- Journal
- Beilstein Journal of Organic Chemistry
- Published
- 2024-09-30
- DOI
- https://doi.org/10.3762/bjoc.20.209
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Université de Pau et des Pays de l'Adour
- Engineering and Physical Sciences Research Council