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Synthesis of alkynes and alkynyl iodides bearing a protected amino alcohol moiety as functionalized amino acids precursors

Science China Chemistry volume 53, pages 1921–1926 (2010)Cite this article

Abstract

Amino acid precursors in protected amino alcohol form are important synthons that can be used as building-blocks for the hemisynthesis of non-natural amino acids. Serine can be used as a common starting material for the synthesis of such compounds differently protected. Particularly, protected amino alcohols bearing an ethynyl and/or an iodoethynyl group can be used in cross-couplings, in 1,3-dipolar cycloadditions and/or in Nozaki-Hiyama-Kishi type reactions. We thus demonstrated that the efficiently protected amino alcohols derived from serine can be coupled to a sugar derivative by an indium mediated alkynylation reaction. The conditions of this coupling are compatible with such functionalized derivatives and allow envisaging an access to C-glycosylated amino acids.

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Authors and Affiliations

  1. Laboratoire de Synthèse Organique Sélective et Chimie bioOrganique-EA 4505, Université de Cergy-Pontoise, F-95000, Cergy-Pontoise, France

    Charfedinne Ayed, Julien Picard, Nadège Lubin-Germain, Jacques Uziel & Jacques Auge

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  1. Charfedinne Ayed
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  2. Julien Picard
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  3. Nadège Lubin-Germain
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  4. Jacques Uziel
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  5. Jacques Auge
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Correspondence to Jacques Uziel or Jacques Auge.

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Ayed, C., Picard, J., Lubin-Germain, N. et al. Synthesis of alkynes and alkynyl iodides bearing a protected amino alcohol moiety as functionalized amino acids precursors. Sci. China Chem. 53, 1921–1926 (2010). https://doi.org/10.1007/s11426-010-4072-2

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  • DOI: https://doi.org/10.1007/s11426-010-4072-2

Keywords

  • amino alcohols
  • amino acids
  • oxazolidines
  • alkynyl iodides
  • C-glycoside
  • indium
  • alkynylation