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

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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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