Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products.

Autor: Montenegro-Sustaita MM; Departamento 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, Mexico., Jiménez-Vázquez HA; Departamento 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, Mexico., Vargas-Díaz E; Departamento 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, Mexico., Herbert-Pucheta JE; Departamento 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, Mexico., Zepeda-Vallejo LG; Departamento 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, Mexico.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2022 Apr 28; Vol. 27 (9). Date of Electronic Publication: 2022 Apr 28.
DOI: 10.3390/molecules27092810
Abstrakt: A representative number of decalin and hydrindane derivatives 2a - l 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 1 H NMR and X-ray crystallography. Such a stereochemical outcome was corroborated by conformational analysis supported by DFT calculations and simulating the 1 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.
Databáze: MEDLINE
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