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Vincek AS, Booth RG. New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate. Tetrahedron Lett. 2009;50(36):5107-5109doi: 10.1016/j.tetlet.2009.06.099.
Vincek, A. S., & Booth, R. G. (2009). New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate. Tetrahedron letters, 50(36), 5107-5109. https://doi.org/10.1016/j.tetlet.2009.06.099
Vincek, Adam S, and Booth, Raymond G. "New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate." Tetrahedron letters vol. 50,36 (2009): 5107-5109. doi: https://doi.org/10.1016/j.tetlet.2009.06.099
Vincek AS, Booth RG. New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate. Tetrahedron Lett. 2009 Sep 09;50(36):5107-5109. doi: 10.1016/j.tetlet.2009.06.099. PMID: 20161011; PMCID: PMC2758692.
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Tetrahedron Lett. 2009 Sep 09;50(36):5107-5109. doi: 10.1016/j.tetlet.2009.06.099.

New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate.

Tetrahedron letters

Adam S Vincek, Raymond G Booth

Affiliations

  1. Department of Medicinal Chemistry, PO Box 100485, College of Pharmacy, University of Florida, Gainesville, FL 32610-0485, USA.

PMID: 20161011 PMCID: PMC2758692 DOI: 10.1016/j.tetlet.2009.06.099

Abstract

Mixed trifluoroacetyl phenylacetyl anhydride and 3-halostyrenes (fluoro, chloro, and bromo) or vinylcycloalkanes (cyclohexyl, cyclooctyl), undergo cascade Friedel-Crafts cycli-acylalkylation, enolization, and O-acylation to give 4-substituted tetralen-2-ol phenylacetates, without additional solvent in good yields. Base alcoholysis of 4-phenyltetralen-2-ol phenylacetate reveals the tetral-2-one for asymmetric transfer hydrogenation. Bromophenyltetralen-2-ol phenylacetate undergoes Suzuki coupling, and provides a short route to trans-4-phenyl-β-aminotetralin.

References

  1. J Org Chem. 2001 Oct 19;66(21):7113-7 - PubMed
  2. J Med Chem. 1993 Aug 20;36(17):2542-51 - PubMed
  3. J Med Chem. 1999 Aug 12;42(16):3041-54 - PubMed
  4. Nature. 2009 Jan 8;457(7226):153-4 - PubMed
  5. Org Lett. 2005 Sep 15;7(19):4177-80 - PubMed
  6. Org Biomol Chem. 2008 Jan 7;6(1):147-50 - PubMed
  7. Pharmacol Biochem Behav. 2008 Nov;91(1):176-80 - PubMed
  8. Angew Chem Int Ed Engl. 1999 Aug;38(16):2413-2416 - PubMed
  9. Bioorg Med Chem. 2006 Oct 1;14(19):6640-58 - PubMed
  10. Farmaco. 2003 Jul;58(7):469-76 - PubMed
  11. J Org Chem. 2006 Jun 23;71(13):4956-64 - PubMed

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