Asymmetric bioreduction of α,β-unsaturated nitriles and ketones

Two applications for the asymmetric reduction of activated alkenes employing isolated enoate reductases are reported. A series of α,β-unsaturated nitriles were shown to be converted to the optically active nitrile products in high yields and excellent enantioselectivities (up to 99% ee). In addition, the reduction of 2,3-disubstituted cyclopentenones was shown to provide almost exclusively trans-2,3-disubstituted cyclopentanones in high yield and enantiopurity (94% ee).

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

2-Phenyl-butyronitrileC10H11N[α]D20=+26.1 (c 7.08, CH3OH)Absolute configuration: (R)-(+)