Asymmetric hydrogenation of the C–C double bond of 1- and 1,2-methylated maleimides with cultured suspension cells of Marchantia polymorpha

Suspension cultured cells of Marchantia polymorpha have the potential to hydrogenate the C–C double bonds of 2-methyl- and 2,3-dimethylmaleimide derivatives to give enantiomerically pure (2R)-2-methyl- and (2R,3R)-2,3-dimethylsuccinimide derivatives, respectively.

Graphical abstractSuspension cultured cells of Marchantia polymorpha have the potential to hydrogenate the C–C double bonds of 2-methyl- and 2,3-dimethylmaleimide derivatives to give enantiomerically pure (2R)-2-methyl- and (2R,3R)-2,3-dimethylsuccinimide derivatives, respectively.Figure optionsDownload full-size imageDownload as PowerPoint slide

N-p-Methoxyphenyl-2-methylsuccinimideC12H13O3NEe = 99%[α]D = +4.0 (c 0.13, CHCl3)Source of chirality: asymm. hydrogenation with the cultured suspension cells of M. polymorphaAbsolute configuration: R

N-Benzyl-2-methylsuccinimideC12H13O2NEe = >99%[α]D = +14.0 (c 0.18, CHCl3)Source of chirality: asymm. hydrogenation with the cultured suspension cells of M. polymorphaAbsolute configuration: R

N-Phenyl-2,3-dimethylsuccinimideC12H13O2NEe = 99%[α]D = +21.0 (c 0.03, CHCl3)Source of chirality: asymm. hydrogenation with the cultured suspension cells of M. polymorphaAbsolute configuration: 2R,3R

N-p-Methoxyphenyl-2,3-dimethylsuccinimideC13H15O3NEe = >99%[α]D = +15.0 (c 0.08, CHCl3)Source of chirality: asymm. hydrogenation with the cultured suspension cells of M. polymorphaAbsolute configuration: 2R,3R