Lipase-catalyzed domino Michael-aldol reaction of 2-methyl-1,3-cycloalkanedione and methyl vinyl ketone for the synthesis of bicyclic compounds
利用統計を見る
Synthesis of bicyclic compounds was achieved via a lipase-catalyzed, stereoselective, domino Michael–aldol reaction of 2-methyl-1,3-cycloalkanedione and methyl vinyl ketone. Appropriate reaction conditions, including the type of enzyme, solvent, and temperature, were determined. In addition, the effects of solvent polarity and addtives were investigated. The reaction proceeded in the presence of lipase AS in a solution of 20% acetone in dimethylsulfoxide (DMSO) at 10 °C for 8 days, followed by the addition of p-toluenesulfonic acid (TsOH) to afford bicyclic compounds in 51–83% yields with moderate stereoselectivity. Although this domino Michael–aldol reaction showed only moderate stereoselectivity, even with the acid-supported enhancement of the reaction, these results represent potential new applications for lipase.
This is an Accepted Manuscript of an article published by Taylor & Francis in Synthetic Communications on 2016, available online: http://wwww.tandfonline.com/10.1080/00397911.2015.1116584.
Lipase-catalyzed domino Michael-aldol reaction of 2-methyl-1,3-cycloalkanedione and methyl vinyl ketone for the synthesis of bicyclic compounds
syc46_1_46.pdf
(441.12KB)
