In the present work, a series of enantiopure homoallylamines were synthesized starting with a Barbier-type indium-mediated allylation of N,N-(dimethysulfamoyl)-protected aldimines followed by high yielding deprotection by transamination affording homoallylamines in good to excellent yields. The racemic homoallylic amines were resolved by lipase catalyzed acylation utilizing acyl donors with a terminal double bond. Finally, the product amide and the enantiopure amine were converted into N-containing heterocycles in a straight-forward mannerutilizing ring-closing metathesis yielding substances mimicking natural products.

Synthesis of enantiopure benzyl homoallylamines by combined Barbier-type allylation/enzymatic kinetic resolution: Toward chemoenzymatic synthesis of <i>N</i>-containing heterocycles

239th National Meeting (2010)

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Synthesis of enantiopure benzyl homoallylamines by combined Barbier-type allylation/enzymatic kinetic resolution: Toward chemoenzymatic synthesis of N-containing heterocycles