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Choucair B, Léon H, Miré MA, et al. Indium- or Zinc-Mediated One-Pot Synthesis of Homoallylamines, beta-Amino Esters, and beta-Amino Nitriles. Org Lett. 2000;2(13):1851-1853doi: 10.1021/ol005912k.
Choucair, B., Léon, H., Miré, M. A., Lebreton, C., & Mosset, P. (2000). Indium- or Zinc-Mediated One-Pot Synthesis of Homoallylamines, beta-Amino Esters, and beta-Amino Nitriles. Organic letters, 2(13), 1851-1853. https://doi.org/10.1021/ol005912k
Choucair, et al. "Indium- or Zinc-Mediated One-Pot Synthesis of Homoallylamines, beta-Amino Esters, and beta-Amino Nitriles." Organic letters vol. 2,13 (2000): 1851-1853. doi: https://doi.org/10.1021/ol005912k
Choucair B, Léon H, Miré MA, Lebreton C, Mosset P. Indium- or Zinc-Mediated One-Pot Synthesis of Homoallylamines, beta-Amino Esters, and beta-Amino Nitriles. Org Lett. 2000 Jun 29;2(13):1851-1853. doi: 10.1021/ol005912k. PMID: 10891174.
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Org Lett. 2000 Jun 29;2(13):1851-1853. doi: 10.1021/ol005912k.

Indium- or Zinc-Mediated One-Pot Synthesis of Homoallylamines, beta-Amino Esters, and beta-Amino Nitriles.

Organic letters

Choucair, Léon, Miré, Lebreton, Mosset

Affiliations

  1. 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.

PMID: 10891174 DOI: 10.1021/ol005912k

Abstract

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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