Indium- or Zinc-Mediated One-Pot Synthesis of Homoallylamines, beta-Amino Esters, and beta-Amino Nitriles.
Homoallylamines, beta-amino esters, and beta-amino nitriles were obtained in a one-pot synthesis directly from an aldehyde and a secondary amine such as dibenzylamine or diallylamine. Their condensation with titanium(IV) isopropoxide generates an intermediate aminoalkoxy titanium complex. Further reaction in THF with nucleophilic organometallic species, generated in situ from indium or zinc and a reactive halide (allyl bromide, alkyl bromo- or iodoacetate, iodoacetonitrile), furnished the corresponding amines.
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Laboratoire de Synthèses et Activations de Biomolécules, CNRS ESA 6052, Ecole Nationale Supérieure de Chimie de Rennes, Avenue du Général Leclerc, F-35700 Rennes, France.
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Miré
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Lebreton
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Mosset
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