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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.
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 uniquely protected. Partlyly, 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 effectively imported amino alcohols derived from serine can be coupled to a sugar derivative by an indium mediated alkynylation reaction. These conditions of this coupling are compatible with such functionalized derivatives and allow envisaging an access to C-glycosylated amino acids.