The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues
The analogous imino-variant of the Nazarov reaction suffers from unfavorable energetics associated with the ring closure process, thereby limiting the utility of this class of reactions. In this report, the realization of the first intermolecular interrupted imino-Nazarov reaction utilizing silylate...
| Main Authors: | , , , |
|---|---|
| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2018
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/90209 http://hdl.handle.net/10220/47208 |
| _version_ | 1811692426321985536 |
|---|---|
| author | William, Ronny Leng, Wei Lin Wang, Siming Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences William, Ronny Leng, Wei Lin Wang, Siming Liu, Xue-Wei |
| author_sort | William, Ronny |
| collection | NTU |
| description | The analogous imino-variant of the Nazarov reaction suffers from unfavorable energetics associated with the ring closure process, thereby limiting the utility of this class of reactions. In this report, the realization of the first intermolecular interrupted imino-Nazarov reaction utilizing silylated pyrimidine derivatives as nucleophilic trapping partners culminated in an expedient synthetic route to carbocyclic nucleoside analogues. The potential application of silylated nucleobases to intercept the oxyallyl cation in other variants of the Nazarov reaction provides vast opportunities to develop new strategies for the formation of carbocyclic nucleoside analogues. |
| first_indexed | 2024-10-01T06:35:36Z |
| format | Journal Article |
| id | ntu-10356/90209 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:35:36Z |
| publishDate | 2018 |
| record_format | dspace |
| spelling | ntu-10356/902092023-02-28T19:36:53Z The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues William, Ronny Leng, Wei Lin Wang, Siming Liu, Xue-Wei School of Physical and Mathematical Sciences Carbocyclic Nucleosides Nazarov Reaction DRNTU::Science::Physics The analogous imino-variant of the Nazarov reaction suffers from unfavorable energetics associated with the ring closure process, thereby limiting the utility of this class of reactions. In this report, the realization of the first intermolecular interrupted imino-Nazarov reaction utilizing silylated pyrimidine derivatives as nucleophilic trapping partners culminated in an expedient synthetic route to carbocyclic nucleoside analogues. The potential application of silylated nucleobases to intercept the oxyallyl cation in other variants of the Nazarov reaction provides vast opportunities to develop new strategies for the formation of carbocyclic nucleoside analogues. MOE (Min. of Education, S’pore) Published version 2018-12-26T08:03:12Z 2019-12-06T17:43:09Z 2018-12-26T08:03:12Z 2019-12-06T17:43:09Z 2016 Journal Article William, R., Leng, W. L., Wang, S., & Liu, X.-W. (2016). The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues. Chemical Science, 7(2), 1100-1103. doi:10.1039/C5SC03559G 2041-6520 https://hdl.handle.net/10356/90209 http://hdl.handle.net/10220/47208 10.1039/C5SC03559G en Chemical Science © 2016 The Author(s) (published by Royal Society of Chemistry). This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. 4 p. application/pdf |
| spellingShingle | Carbocyclic Nucleosides Nazarov Reaction DRNTU::Science::Physics William, Ronny Leng, Wei Lin Wang, Siming Liu, Xue-Wei The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues |
| title | The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues |
| title_full | The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues |
| title_fullStr | The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues |
| title_full_unstemmed | The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues |
| title_short | The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues |
| title_sort | first intermolecular interrupted imino nazarov reaction expeditious access to carbocyclic nucleoside analogues |
| topic | Carbocyclic Nucleosides Nazarov Reaction DRNTU::Science::Physics |
| url | https://hdl.handle.net/10356/90209 http://hdl.handle.net/10220/47208 |
| work_keys_str_mv | AT williamronny thefirstintermolecularinterruptediminonazarovreactionexpeditiousaccesstocarbocyclicnucleosideanalogues AT lengweilin thefirstintermolecularinterruptediminonazarovreactionexpeditiousaccesstocarbocyclicnucleosideanalogues AT wangsiming thefirstintermolecularinterruptediminonazarovreactionexpeditiousaccesstocarbocyclicnucleosideanalogues AT liuxuewei thefirstintermolecularinterruptediminonazarovreactionexpeditiousaccesstocarbocyclicnucleosideanalogues AT williamronny firstintermolecularinterruptediminonazarovreactionexpeditiousaccesstocarbocyclicnucleosideanalogues AT lengweilin firstintermolecularinterruptediminonazarovreactionexpeditiousaccesstocarbocyclicnucleosideanalogues AT wangsiming firstintermolecularinterruptediminonazarovreactionexpeditiousaccesstocarbocyclicnucleosideanalogues AT liuxuewei firstintermolecularinterruptediminonazarovreactionexpeditiousaccesstocarbocyclicnucleosideanalogues |