Enzyme-catalyzed asymmetric construction of chiral tertiary alcohols via aldol reaction using proteinase

• Chiral tertiary alcohols were obtained via asymmetric ketone–ketone aldol reaction.
• Proteinase from Aspergillus melleus (AMP) was used as a sustainable biocatalyst.
• Enzymatic promiscuity was used to construct chiral tertiary alcohols.
• This work expands the application of natural enzyme in organic synthesis.

A new enzyme-catalyzed asymmetric construction of chiral tertiary alcohols via asymmetric aldol reactions between β,γ-unsaturated α-keto esters and ketones was reported. Proteinase from Aspergillus melleus (AMP) was used as a sustainable biocatalyst. The best results can be obtained with yields of up to 90%, diastereoselectives of up to 93:7 dr, and enantioselectivities of up to 70% ee. This work not only expands the application of enzymatic promiscuity, but also provides more examples for constructing chiral tertiary alcohols.

Figure optionsDownload as PowerPoint slideChiral tertiary alcohol was obtained via asymmetric ketone–ketone aldol reaction using proteinase from Aspergillus melleus (AMP) as a sustainable biocatalyst.