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

Catherine A. Faler and Madeleine M. Joullié*
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
Org. Lett., 2007, 9 (10), pp 1987–1990
DOI: 10.1021/ol0705907
Publication Date (Web): April 21, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mjoullie@sas.upenn.edu

Abstract

Abstract Image

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.

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  • Published In Issue May 10, 2007
  • Received March 9, 2007

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