17553-89-8Relevant articles and documents
Desymmetrisation of: Meso -diones promoted by a highly recyclable polymer-supported chiral phosphoric acid catalyst
Clot-Almenara, Lidia,Rodríguez-Escrich, Carles,Pericàs, Miquel A.
, p. 6910 - 6914 (2018/02/23)
A polystyrene-supported BINOL-derived chiral phosphoric acid has been applied to the desymmetrisation of meso-diones to produce enantioenriched cyclohexenones. The catalytic resin has proven highly active and robust, giving rise to Hajos-Parrish or Wieland-Miescher type products in good yields and enantioselectivities, while allowing for extended recycling.
Lipase-catalyzed domino Michael-aldol reaction of 2-methyl-1,3-cycloalkanedione and methyl vinyl ketone for the synthesis of bicyclic compounds
Sano, Kaoru,Kohari, Yoshihito,Nakano, Hiroto,Seki, Chigusa,Takeshita, Mitsuhiro,Tokiwa, Micho,Hirose, Yoshihiko,Uwai, Koji
, p. 46 - 54 (2016/01/09)
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.
A practical protocol for asymmetric synthesis of wieland-miescher and hajos-parrish ketones catalyzed by a simple chiral primary amine
Xu, Changming,Zhang, Long,Zhou, Pengxin,Luo, Sanzhong,Cheng, Jin-Pei
, p. 1939 - 1945 (2013/07/26)
This article describes a simple chiral primary amine catalyzed efficient and practical protocol for the large-scale synthesis of Wieland-Miescher and Hajos-Parrish ketones as well as their analogues. Georg Thieme Verlag Stuttgart. New York.