Highly Enantioselective Synthesis of β-Amino Alcohols:  A Catalytic Version

Thomas-Xavier Métro, Domingo Gomez Pardo,* and Janine Cossy*;
Laboratoire de Chimie Organique, ESPCI-ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France
J. Org. Chem., 2007, 72 (17), pp 6556–6561
DOI: 10.1021/jo071028x
Publication Date (Web): July 21, 2007
Copyright © 2007 American Chemical Society

Abstract

Abstract Image

Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of trifluoroacetic anhydride.

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This article has been cited by 7 ACS Journal articles (5 most recent appear below).

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      Organic Letters2011 Article ASAP

      Herein we report a novel methodology for the asymmetric synthesis of 3-substituted piperidines from readily available chiral building blocks. This method, which features a novel irreversible dihydropyrole-tetrahydropyridine ring expansion, allows the ...

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    One-Pot Stereoselective Synthesis of 1,2-Amino Alcohol Derivatives

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    • One-Pot Stereoselective Synthesis of 1,2-Amino Alcohol Derivatives

      Alicia Boto and Iván Romero-Estudillo
      Organic Letters2011 Article ASAP

      Common β-hydroxy amino acids (such as threonine) can be readily transformed into 1,2-amino alcohols with excellent stereoselectivity. This one-pot decarboxylation–alkylation process allows the replacement of the carboxyl group by alkyl, allyl, or aryl ...

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    Asymmetric Synthesis of an Antagonist of Neurokinin Receptors: SSR 241586

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    • Asymmetric Synthesis of an Antagonist of Neurokinin Receptors: SSR 241586

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      The Journal of Organic Chemistry2011 76 (8), 2594-2602

      SSR 241586 is a 2,2-disubstituted morpholine, developed by Sanofi-Aventis, which is active in the treatment of schizophrenia and irritable bowel syndrome (IBS). Different strategies have been studied to synthesize this molecule and among the strategies an ...

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    Assessing the Rates of Ring-Opening of Aziridinium and Azetidinium Ions: A Dramatic Ring Size Effect

    Nicolas De Rycke, Olivier David, and François Couty
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    • Assessing the Rates of Ring-Opening of Aziridinium and Azetidinium Ions: A Dramatic Ring Size Effect

      Nicolas De Rycke, Olivier David, and François Couty
      Organic Letters2011 13 (7), 1836-1839

      Rates for the ring-opening of aziridinium and azetidinium ions by DMAP were measured. The four-membered ring appears to be ca. 17 000 times less reactive compared to the three-membered ring but is still highly relevant from a synthetic viewpoint. The ...

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History

  • Published In Issue August 17, 2007
  • Received May 16, 2007

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