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.

Pepsin 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 as PowerPoint slide