Work

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

Year: 2024

Type: article

Abstract: A change in mechanism was observed in the hypervalent iodine mediated cyclization of N-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.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.20.209

Authors: Smaher E Butt, Konrad Kepski, Jean-Marc Sotiropoulos, Wesley J Moran

Institutions: University of Huddersfield, Centre National de la Recherche Scientifique, Université de Pau et des Pays de l'Adour, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux, Keele University

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Université de Pau et des Pays de l'Adour, Engineering and Physical Sciences Research Council

Award: DTP 2020-2021 University of Huddersfield