Gaëlle Malik

Publications (3)14.25 Total impact

• Article: Synthesis of β-Hydroxy O-Alkyl Hydroxylamines from Epoxides Using a Convenient and Versatile Two-Step Procedure

  Gaëlle Malik, Angélique Ferry, Xavier Guinchard, David Crich
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  ABSTRACT: A simple and convenient synthetic method was developed to prepare β-hydroxy O-alkyl hydroxylamines in which base-mediated ring opening of epoxides with acetophenone oxime followed by cleavage of the oxime with 2,4-dinitrophenylhydrazine in acidic media furnished the hydroxylamine, which can be protected in situ with various N-protecting groups.
  Synthesis 01/2013; 45(1):65-74. · 2.47 Impact Factor
• Article: NO Bond as a Glycosidic-Bond Surrogate: Synthetic Studies Toward Polyhydroxylated N-Alkoxypiperidines.

  Gaëlle Malik, Angélique Ferry, Xavier Guinchard, Thierry Cresteil, David Crich
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  ABSTRACT: A series of novel polyhydroxylated N-alkoxypiperidines has been synthesized by ring-closing double reductive amination (DRA) of highly functionalized 1,5-dialdehydes with various hydroxylamines. The required saccharide-based dialdehydes were prepared efficiently from sodium cyclopentadienylide in seven steps. A two-step protocol has been developed for the DRA; it led, after deprotection, to isofagomine, 3-deoxyisofagomine, and numerous other N-alkoxy analogues. The barrier to inversion in these polyhydroxylated N-alkoxypiperidine derivatives was found by variable-temperature NMR methods to be approximately 15 kcal mol(-1) . With the exception of N-hydroxyisofagomine itself, none of the compounds prepared showed significant inhibitory activity against sweet almond β-glucosidase.
  Chemistry 12/2012; · 5.93 Impact Factor
• Article: Asymmetric synthesis of polyhydroxylated N-alkoxypiperidines by ring-closing double reductive amination: facile preparation of isofagomine and analogues.

  Gaëlle Malik, Xavier Guinchard, David Crich
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  ABSTRACT: A de novo synthesis of novel polyhydroxylated N-alkoxypiperidines based on the ring-closing double reductive amination of 1,5-dialdehydes, obtained by oxidative cleavage of cyclopentene derivatives, with O-substituted hydroxylamines is reported. Isofagomine was accessed by cleavage of the N-O bond of an N-alkoxypiperidine.
  Organic Letters 12/2011; 14(2):596-9. · 5.86 Impact Factor