Abstract
Methyl α-cyano β-(hetero)aryl acrylates are excellent substrates for CAL-B catalyzed aminolyses. However, upon concatenation of the substrate Knoevenagel condensation (of (hetero)aryl carbaldehydes and methyl cyano acetate) and the CAL-B catalyzed aminolysis, an interesting bifurcating domino Knoevenagel-CAL-B catalyzed aryl methylaminolysis/hydrolysis reaction furnishing either amides or salts in the sense of a three-component process was found. The enzyme mediated acylative bifurcation of water vs benzyl amines depends on the substitution pattern of the aldehydes and on the presence or absence of a water scavenger. In the former case, amidation is favored while in the latter case hydrolysis/salt formation prevails.
Keywords: Aldol condensation, amidation, chemoenzymatic reaction, domino reaction, hydrolysis, lipase, protonolysis.
Graphical Abstract
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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