Asymmetric Morita–Baylis–Hillman reaction catalyzed by pepsin

•Pepsin-catalyzed Morita–Baylis–Hillman (MBH) reaction was described.•15 examples of MBH products were obtained by this reaction.•The novel reaction also expands the field of organic synthesis.•This work promotes the development of enzyme catalytic promiscuity.

Pepsin from porcine gastric mucous shown catalytic promiscuity was first discovered to catalyze the Morita–Baylis–Hillman (MBH) reaction between aromatic aldehydes with 2-cyclohexen-1-one or 2-cyclopenten-1-one in a two-phase medium of phosphate buffer/cyclohexane in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO). The best results of the corresponding MBH products up to 77% yield and 38% ee were achieved.

Graphical abstractPepsin from porcine gastric mucous shown catalytic promiscuity was first used to catalyze Morita–Baylis–Hillman reaction in combination with 1,4-diazabicyclo[2.2.2]octane (DABCO).Figure optionsDownload full-size imageDownload as PowerPoint slide