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高价碘介导的双高烯丙基酰胺环化生成脯氨醇。

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols.

作者信息

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

机构信息

Department of Physical and Life Sciences, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, United Kingdom.

Université de Pau et des Pays de l'Adour, IPREM (CNRS-UMR 5254), Technopole Hélioparc, 2 Avenue du Président Pierre Angot, 64053 Pau Cedex 09, France.

出版信息

Beilstein J Org Chem. 2024 Sep 30;20:2455-2460. doi: 10.3762/bjoc.20.209. eCollection 2024.

DOI:10.3762/bjoc.20.209
PMID:39376490
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11457059/
Abstract

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

摘要

当烯烃与酰胺之间的碳链从两个原子增加到三个原子时，在高价碘介导的-烯基酰胺环化反应中观察到了反应机理的变化。在后一种情况下，酰胺氮上的环化形成吡咯烷环比酰胺氧上的环化更有利。进行了一项密度泛函理论（DFT）研究，以阐明这种环化过程机理的变化。此外，还开发了反应条件，并研究了这种环化反应的适用范围。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/701701d55c96/Beilstein_J_Org_Chem-20-2455-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/a25a9805c51d/Beilstein_J_Org_Chem-20-2455-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/9ce764ffd828/Beilstein_J_Org_Chem-20-2455-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/ac9d55952728/Beilstein_J_Org_Chem-20-2455-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/d40c05f3487e/Beilstein_J_Org_Chem-20-2455-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/701701d55c96/Beilstein_J_Org_Chem-20-2455-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/a25a9805c51d/Beilstein_J_Org_Chem-20-2455-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/9ce764ffd828/Beilstein_J_Org_Chem-20-2455-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/ac9d55952728/Beilstein_J_Org_Chem-20-2455-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/d40c05f3487e/Beilstein_J_Org_Chem-20-2455-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a6ac/11457059/701701d55c96/Beilstein_J_Org_Chem-20-2455-g006.jpg

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