@article{oai:muroran-it.repo.nii.ac.jp:00008604, author = {SANO, Kaoru and 佐野, 薫 and KOHARI, Yoshihito and 小針, 良仁 and 中野, 博人 and NAKANO, Hiroto and SEKI, Chigusa and 関, 千草 and TAKESHITA, Mitsuhiro and 竹下, 光弘 and TOKIWA, Michio and 常盤, 峻士 and HIROSE, Yoshihiko and 廣瀬, 芳彦 and UWAI, Koji and 上井, 幸司}, issue = {1}, journal = {Synthetic Communications}, month = {}, note = {application/pdf, 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.}, pages = {46--54}, title = {Lipase-catalyzed domino Michael-aldol reaction of 2-methyl-1,3-cycloalkanedione and methyl vinyl ketone for the synthesis of bicyclic compounds}, volume = {46}, year = {2016}, yomi = {サノ, カオル and コハリ, ヨシヒト and ナカノ, ヒロト and セキ, チグサ and タケシタ, ミツヒロ and トキワ, ミチオ and ヒロセ, ヨシヒコ and ウワイ, コウジ} }