Cargando…
Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions
The ortho-nitro effect was discovered in sulfa-Staudinger cycloadditions of ethoxycarbonylsulfene with linear imines. When an ortho-nitro group is present at the C-aryl substituents of linear imines, the sulfa-Staudinger cycloadditions deliver cis-β-sultams in considerable amounts, together with the...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154622/ https://www.ncbi.nlm.nih.gov/pubmed/28498354 http://dx.doi.org/10.3390/molecules22050784 |
_version_ | 1783357726486691840 |
---|---|
author | Yang, Zhanhui Abdellaoui, Hassane He, Wei Xu, Jiaxi |
author_facet | Yang, Zhanhui Abdellaoui, Hassane He, Wei Xu, Jiaxi |
author_sort | Yang, Zhanhui |
collection | PubMed |
description | The ortho-nitro effect was discovered in sulfa-Staudinger cycloadditions of ethoxycarbonylsulfene with linear imines. When an ortho-nitro group is present at the C-aryl substituents of linear imines, the sulfa-Staudinger cycloadditions deliver cis-β-sultams in considerable amounts, together with the predominant trans-β-sultams. In other cases, the above sulfa-Staudinger cycloadditions give rise to trans-β-sultams exclusively. Further mechanistic rationalization discloses that the ortho-nitro effect is attributed to its strong electron-withdrawing inductive effect. Similarly, the ortho-nitro effect also exists in Staudinger cycloadditions of ethoxycarbonyl ketene with the imines. The current research provides further insights into the diastereoselective control in sulfa-Staudinger and Staudinger cycloadditions. |
format | Online Article Text |
id | pubmed-6154622 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61546222018-11-13 Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions Yang, Zhanhui Abdellaoui, Hassane He, Wei Xu, Jiaxi Molecules Article The ortho-nitro effect was discovered in sulfa-Staudinger cycloadditions of ethoxycarbonylsulfene with linear imines. When an ortho-nitro group is present at the C-aryl substituents of linear imines, the sulfa-Staudinger cycloadditions deliver cis-β-sultams in considerable amounts, together with the predominant trans-β-sultams. In other cases, the above sulfa-Staudinger cycloadditions give rise to trans-β-sultams exclusively. Further mechanistic rationalization discloses that the ortho-nitro effect is attributed to its strong electron-withdrawing inductive effect. Similarly, the ortho-nitro effect also exists in Staudinger cycloadditions of ethoxycarbonyl ketene with the imines. The current research provides further insights into the diastereoselective control in sulfa-Staudinger and Staudinger cycloadditions. MDPI 2017-05-12 /pmc/articles/PMC6154622/ /pubmed/28498354 http://dx.doi.org/10.3390/molecules22050784 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Yang, Zhanhui Abdellaoui, Hassane He, Wei Xu, Jiaxi Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions |
title | Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions |
title_full | Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions |
title_fullStr | Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions |
title_full_unstemmed | Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions |
title_short | Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions |
title_sort | ortho-nitro effect on the diastereoselective control in sulfa-staudinger and staudinger cycloadditions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154622/ https://www.ncbi.nlm.nih.gov/pubmed/28498354 http://dx.doi.org/10.3390/molecules22050784 |
work_keys_str_mv | AT yangzhanhui orthonitroeffectonthediastereoselectivecontrolinsulfastaudingerandstaudingercycloadditions AT abdellaouihassane orthonitroeffectonthediastereoselectivecontrolinsulfastaudingerandstaudingercycloadditions AT hewei orthonitroeffectonthediastereoselectivecontrolinsulfastaudingerandstaudingercycloadditions AT xujiaxi orthonitroeffectonthediastereoselectivecontrolinsulfastaudingerandstaudingercycloadditions |