Aldol condensation versus conjugate addition: intramolecular cyclization using a combination of Lewis acid and 1,2-diol.
The reactivity of 3-substituted 4-methyl-4-(3-oxobutyl)-2-cyclohexen-1-ones (1) in the presence of a combination of a Lewis acid and a 1,2-diol was studied. The results suggest several factors that influence 6-membered ring formation, including two types of intramolecular aldol reaction and intramolecular 1,4-addition, due to the C3-substituent, Lewis acid, and the presence of diol. In this study, novel methodology to prepare two types of decalin skeleton could be developed.
Yamada
S
S
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Suemune
H
H
D000143:Acids / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D013057:Spectrum Analysis
D000143:Acids; D000447:Aldehydes