Hypervalent iodine mediated cyclization of bishomoallylamides to prolinols

Submitting author affiliation:
Keele University, Keele, United Kingdom

Beilstein Arch. 2024, 202431. https://doi.org/10.3762/bxiv.2024.31.v1

Published 14 May 2024

cc-by Logo
This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


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.

Keywords: Hypervalent iodine; cyclization; proline; DFT; mechanism

Supporting Information

Format: DOCX Size: 5.7 MB   Download

How to Cite

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:

Butt, S. E.; Kepski, K.; Sotiropoulos, J.-M.; Moran, W. J. Beilstein Arch. 2024, 202431. doi:10.3762/bxiv.2024.31.v1

Download Citation

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.