Synthesis of Enantiopure Benzyl Homoallylamines by Indium‐Mediated Barbier‐Type Allylation Combined with Enzymatic Kinetic Resolution: Towards the Chemoenzymatic Synthesis of N‐Containing Heterocycles

Abstract

AbstractBarbier‐type indium‐mediated allylations of different N,N‐(dimethylsulfamoyl)‐protected aldimines with a number of allyl bromides followed by high‐yielding deprotection afforded allylic amines in good to excellent yields. The racemic amines were then subjected to enzymatic kinetic resolution in order to obtain the corresponding (S)‐amines and (R)‐amides. When acyl donors with a terminal double bond were applied in the enzymatic kinetic resolution, the product amide could be converted into unsaturated lactams in a straightforward manner by utilizing ring‐closing metathesis. Furthermore, the enantiopure (S)‐1‐phenylbut‐3‐enylamine was converted into the corresponding diallylamine, which was subjected to ring‐closing metathesis to yield a substituted dehydropiperidine mimicking a number of natural products.