TY - JOUR
T1 - Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products
AU - Montenegro-Sustaita, Mabel M.
AU - Jiménez-Vázquez, Hugo A.
AU - Zepeda-Vallejo, L. Gerardo
AU - Vargas-Díaz, Elena
AU - Herbert-Pucheta, J. Enrique
N1 - Publisher Copyright:
© 2022 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2022/5/1
Y1 - 2022/5/1
N2 - 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 the1 H NMR and X-ray crystallography. Such a stereochemical outcome was corroborated by conformational analysis supported by DFT calculations and simulating the1 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.
AB - 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 the1 H NMR and X-ray crystallography. Such a stereochemical outcome was corroborated by conformational analysis supported by DFT calculations and simulating the1 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.
KW - cycloalkanone enolates
KW - decalin/hydrindane derivatives
KW - double Michael addition
KW - methyl acrylate
KW - stereochemical outcome
UR - http://www.scopus.com/inward/record.url?scp=85129886001&partnerID=8YFLogxK
U2 - 10.3390/molecules27092810
DO - 10.3390/molecules27092810
M3 - Artículo
C2 - 35566162
AN - SCOPUS:85129886001
SN - 1420-3049
VL - 27
JO - Molecules
JF - Molecules
IS - 9
M1 - 2810
ER -