Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products
A representative number of decalin and hydrindane derivatives <b>2a</b>–<b>l</b> were prepared in 11–91% yield by means of a cascade reaction of cyclohexanone/cyclopentanone enolates and methyl acrylate through a Michael–Michael ring closure (MIMIRC) process. The relative ste...
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MDPI AG
2022-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/9/2810 |
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| author | Mabel M. Montenegro-Sustaita Hugo A. Jiménez-Vázquez Elena Vargas-Díaz J. Enrique Herbert-Pucheta L. Gerardo Zepeda-Vallejo |
| author_facet | Mabel M. Montenegro-Sustaita Hugo A. Jiménez-Vázquez Elena Vargas-Díaz J. Enrique Herbert-Pucheta L. Gerardo Zepeda-Vallejo |
| author_sort | Mabel M. Montenegro-Sustaita |
| collection | DOAJ |
| description | A representative number of decalin and hydrindane derivatives <b>2a</b>–<b>l</b> were prepared in 11–91% yield by means of a cascade reaction of cyclohexanone/cyclopentanone enolates and methyl acrylate through a Michael–Michael ring closure (MIMIRC) process. The relative stereochemistry of the four stereogenic centers formed in all products was determined by analyzing the vicinal coupling constants from the <sup>1</sup>H NMR and X-ray crystallography. Such a stereochemical outcome was corroborated by conformational analysis supported by DFT calculations and simulating the <sup>1</sup>H NMR spectra of representative products. All products showed the same relative stereochemistry at C-1 and C-8a, while at C-3 and bridgehead carbon C-4a, configurational changes were observed. The present results provide some insights about the scope and limitations of the triple cascade reaction between cycloalkanone enolates with methyl acrylate. This synthetic protocol is still a simple and very practical alternative to generate decalin and hydrindane derivatives with great structural diversity. |
| first_indexed | 2024-03-10T03:54:43Z |
| format | Article |
| id | doaj.art-856646ed6a2f4cfa8545c4d437456e82 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:54:43Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-856646ed6a2f4cfa8545c4d437456e822023-11-23T08:50:00ZengMDPI AGMolecules1420-30492022-04-01279281010.3390/molecules27092810Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction ProductsMabel M. Montenegro-Sustaita0Hugo A. Jiménez-Vázquez1Elena Vargas-Díaz2J. Enrique Herbert-Pucheta3L. Gerardo Zepeda-Vallejo4Departamento de Química Orgánica, Instituto Politécnico Nacional, Escuela Nacional de Ciencias Biológicas, Prolongación de Carpio y Plan de Ayala s/n, Col. Santo Tomas., Alc. Miguel Hidalgo, Ciudad de México 11340, MexicoDepartamento de Química Orgánica, Instituto Politécnico Nacional, Escuela Nacional de Ciencias Biológicas, Prolongación de Carpio y Plan de Ayala s/n, Col. Santo Tomas., Alc. Miguel Hidalgo, Ciudad de México 11340, MexicoDepartamento de Química Orgánica, Instituto Politécnico Nacional, Escuela Nacional de Ciencias Biológicas, Prolongación de Carpio y Plan de Ayala s/n, Col. Santo Tomas., Alc. Miguel Hidalgo, Ciudad de México 11340, MexicoDepartamento de Química Orgánica, Instituto Politécnico Nacional, Escuela Nacional de Ciencias Biológicas, Prolongación de Carpio y Plan de Ayala s/n, Col. Santo Tomas., Alc. Miguel Hidalgo, Ciudad de México 11340, MexicoDepartamento de Química Orgánica, Instituto Politécnico Nacional, Escuela Nacional de Ciencias Biológicas, Prolongación de Carpio y Plan de Ayala s/n, Col. Santo Tomas., Alc. Miguel Hidalgo, Ciudad de México 11340, MexicoA representative number of decalin and hydrindane derivatives <b>2a</b>–<b>l</b> were prepared in 11–91% yield by means of a cascade reaction of cyclohexanone/cyclopentanone enolates and methyl acrylate through a Michael–Michael ring closure (MIMIRC) process. The relative stereochemistry of the four stereogenic centers formed in all products was determined by analyzing the vicinal coupling constants from the <sup>1</sup>H NMR and X-ray crystallography. Such a stereochemical outcome was corroborated by conformational analysis supported by DFT calculations and simulating the <sup>1</sup>H NMR spectra of representative products. All products showed the same relative stereochemistry at C-1 and C-8a, while at C-3 and bridgehead carbon C-4a, configurational changes were observed. The present results provide some insights about the scope and limitations of the triple cascade reaction between cycloalkanone enolates with methyl acrylate. This synthetic protocol is still a simple and very practical alternative to generate decalin and hydrindane derivatives with great structural diversity.https://www.mdpi.com/1420-3049/27/9/2810decalin/hydrindane derivativesdouble Michael additionmethyl acrylatecycloalkanone enolatesstereochemical outcome |
| spellingShingle | Mabel M. Montenegro-Sustaita Hugo A. Jiménez-Vázquez Elena Vargas-Díaz J. Enrique Herbert-Pucheta L. Gerardo Zepeda-Vallejo Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products Molecules decalin/hydrindane derivatives double Michael addition methyl acrylate cycloalkanone enolates stereochemical outcome |
| title | Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products |
| title_full | Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products |
| title_fullStr | Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products |
| title_full_unstemmed | Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products |
| title_short | Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products |
| title_sort | structural analysis of the michael michael ring closure mimirc reaction products |
| topic | decalin/hydrindane derivatives double Michael addition methyl acrylate cycloalkanone enolates stereochemical outcome |
| url | https://www.mdpi.com/1420-3049/27/9/2810 |
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