Synthesis of Bicyclic Cyclopropyl- amines from Amino Acid Derivatives

The synthesis of novel [3.1.0]bicyclic cyclopropylamines from differently substituted amino acids using Ti(II)-mediated coupling and the extension of this methodology to provide [4.1.0]systems is described.Cyclopropylamines and substituted cyclopropylamines are important structural elements in a variety of biologically active compounds.We have previously reported the Ti(II)-mediated coupling of a terminal olefin and the N,N'-dimethyl carboxamide moiety of aromatic amino acid derivatives to synthesize a series of N, N'-dimethylcyclopropylamines, by applying the Kulinkovich reaction to modified amino acids, and found that a tyrosine derivative was a weak dopamine receptor antagonist. 1 Here, we present