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The Kulinkovich Reaction in the Synthesis of Constrained N,N-Dialkyl Neurotransmitter Analogues

Catherine A. Faler and Madeleine M. Joulliť*

*Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, Email:

C. A. Faler, M. M. Joulliť, Org. Lett., 2007, 9, 1987-1990.

DOI: 10.1021/ol0705907

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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 potent inhibitors of monoamine oxidase were made in 1 to 5 steps from readily available starting materials and have been shown to mimic hallucinogens.

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Key Words

Kulinkovich-de Meijere Reaction

ID: J54-Y2007-1500