11.1.2  Reactions with Amines

Optically pure amines serve as versatile intermediates in the manufacture of pharmaceuticals and agrochemicals. The lipase-catalyzed acylation of amines proceeds efficiently with excellent enantioselectivity (Scheme 4). In this reaction, one of the enantiomer is converted into amide and the remaining amine enantiomer can be obtained in enantiomerically enriched form. The reaction functions in organic medium, MTBE as solvent, and E value exceeds 2000 (E = environmentally impact of the process).

Scheme 4

11.1.3  Other Acylations

Enzymatic catalytic transformation of achiral amines and racemic acid components known as aminolysis affords elegant approach for the synthesis of enantioenriched acids. An interesting example is the reaction of dimethyl 3-(benzylamino)glutarate to give monoamides with excellent enantioselectivity (Scheme 5). The monoamides are intermediates for the synthesis of unnatural β -amino acids.

Scheme 5