10.1002/ejoc.200901216
The research explores a chemoenzymatic approach to synthesize enantiopure benzyl homoallylamines and their subsequent transformation into N-containing heterocycles. The purpose of this study is to develop a reliable and efficient method for producing enantiopure amines, which are crucial intermediates in the synthesis of biologically and pharmaceutically relevant compounds, such as neuroactive pharmaceuticals and peptidomimetics. The researchers utilized indium-mediated Barbier-type allylation of N,N-dimethylsulfamoyl-protected aldimines to produce racemic homoallylamines. These were then subjected to enzymatic kinetic resolution using lipase-catalyzed N-acylation to obtain enantiopure (S)-amines and (R)-amides. The enantiopure amines were further converted into N-containing heterocycles through ring-closing metathesis. Key chemicals used in this research include indium, various allylating agents (e.g., methallyl bromide, prenyl bromide), N,N-dimethylsulfamoyl-protected aldimines, lipase enzymes (e.g., Burkholderia cepacia lipase, Candida antarctica lipases), and acyl donors (e.g., ethyl methoxyacetate, isopropyl acetate). The study concludes that this combined chemoenzymatic approach is effective for synthesizing enantiopure amines and N-containing heterocycles, demonstrating its potential for creating biologically active compounds with high enantiopurity.
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