Copper-Catalyzed Four-Component A<sup>3</sup>-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived Spirocycles
3-Oxetanone-derived spirooxazolidines represent a class of building blocks for accessing diverse saturated heterocycles, but their synthetic methods remain unexplored. Herein, we demonstrate a highly atom-economic approach for the synthesis of diverse 3-oxetanone-derived <i>N</i>-proparg...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-02-01
|
| Series: | Chemistry |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2624-8549/7/1/19 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849720222344282112 |
|---|---|
| author | Rongkang Zhang Liliang Huang Aiguo Gu Huangdi Feng |
| author_facet | Rongkang Zhang Liliang Huang Aiguo Gu Huangdi Feng |
| author_sort | Rongkang Zhang |
| collection | DOAJ |
| description | 3-Oxetanone-derived spirooxazolidines represent a class of building blocks for accessing diverse saturated heterocycles, but their synthetic methods remain unexplored. Herein, we demonstrate a highly atom-economic approach for the synthesis of diverse 3-oxetanone-derived <i>N</i>-propargyl spirooxazolidines via a CuBr<sub>2</sub>/TFA co-catalyzed four-component A<sup>3</sup>-based cascade reaction of a 1,2-amino alcohol, a 3-oxetanone, a formaldehyde, and an alkyne. This strategy is characterized by a wide substrate range and excellent chemoselectivity. In addition, the synthesized spirocycles could also be easily converted into other valuable compounds, facilitating potentially useful synthetic applications. |
| format | Article |
| id | doaj-art-e6929c42d5094ae5921750ec68664889 |
| institution | DOAJ |
| issn | 2624-8549 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry |
| spelling | doaj-art-e6929c42d5094ae5921750ec686648892025-08-20T03:11:59ZengMDPI AGChemistry2624-85492025-02-01711910.3390/chemistry7010019Copper-Catalyzed Four-Component A<sup>3</sup>-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived SpirocyclesRongkang Zhang0Liliang Huang1Aiguo Gu2Huangdi Feng3College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, ChinaCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, ChinaJiangsu Product Quality Testing & Inspection Institute, 5 Guanghua Street, Nanjing 210007, ChinaCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China3-Oxetanone-derived spirooxazolidines represent a class of building blocks for accessing diverse saturated heterocycles, but their synthetic methods remain unexplored. Herein, we demonstrate a highly atom-economic approach for the synthesis of diverse 3-oxetanone-derived <i>N</i>-propargyl spirooxazolidines via a CuBr<sub>2</sub>/TFA co-catalyzed four-component A<sup>3</sup>-based cascade reaction of a 1,2-amino alcohol, a 3-oxetanone, a formaldehyde, and an alkyne. This strategy is characterized by a wide substrate range and excellent chemoselectivity. In addition, the synthesized spirocycles could also be easily converted into other valuable compounds, facilitating potentially useful synthetic applications.https://www.mdpi.com/2624-8549/7/1/19spirocycleoxetanoneoxazolidinemulticomponent reactiondomino reaction |
| spellingShingle | Rongkang Zhang Liliang Huang Aiguo Gu Huangdi Feng Copper-Catalyzed Four-Component A<sup>3</sup>-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived Spirocycles Chemistry spirocycle oxetanone oxazolidine multicomponent reaction domino reaction |
| title | Copper-Catalyzed Four-Component A<sup>3</sup>-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived Spirocycles |
| title_full | Copper-Catalyzed Four-Component A<sup>3</sup>-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived Spirocycles |
| title_fullStr | Copper-Catalyzed Four-Component A<sup>3</sup>-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived Spirocycles |
| title_full_unstemmed | Copper-Catalyzed Four-Component A<sup>3</sup>-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived Spirocycles |
| title_short | Copper-Catalyzed Four-Component A<sup>3</sup>-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived Spirocycles |
| title_sort | copper catalyzed four component a sup 3 sup based cascade reaction facile synthesis of 3 oxetanone derived spirocycles |
| topic | spirocycle oxetanone oxazolidine multicomponent reaction domino reaction |
| url | https://www.mdpi.com/2624-8549/7/1/19 |
| work_keys_str_mv | AT rongkangzhang coppercatalyzedfourcomponentasup3supbasedcascadereactionfacilesynthesisof3oxetanonederivedspirocycles AT lilianghuang coppercatalyzedfourcomponentasup3supbasedcascadereactionfacilesynthesisof3oxetanonederivedspirocycles AT aiguogu coppercatalyzedfourcomponentasup3supbasedcascadereactionfacilesynthesisof3oxetanonederivedspirocycles AT huangdifeng coppercatalyzedfourcomponentasup3supbasedcascadereactionfacilesynthesisof3oxetanonederivedspirocycles |