Organic Letters 2007-05-10

The Kulinkovich reaction in the synthesis of constrained n,n-dialkyl neurotransmitter analogues.

Catherine A Faler, Madeleine M Joullié

Index: Org. Lett. 9(10) , 1987-90, (2007)

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Abstract

An intermolecular Ti(IV)-mediated cyclopropanation reaction has been used to synthesize substituted 2-phenylcyclopropylamines and constrained analogues of the neurotransmitters histamine and tryptamine. Many hydroxy- and methoxy-substituted phenylcyclopropylamines are known to inhibit monoamine oxidase and have been shown to mimic hallucinogens. These compounds were made in 1 to 5 steps from readily available starting materials.