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

作　　者：AYED Charfedinne PICARD Julien LUBIN-GERMAIN Nadège UZIEL Jacques AUGE Jacques 

机构地区：[1]Université de Cergy-Pontoise,Laboratoire de Synthèse Organique Sélective et Chimie bioOrganique-EA 4505

出　　处：《Science China Chemistry》2010年第9期1921-1926,共6页中国科学（化学英文版）

摘　　要：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 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.

关 键 词：AMINO alcohols AMINO acids OXAZOLIDINES ALKYNYL IODIDES C-GLYCOSIDE indium ALKYNYLATION 

分 类 号：O621.3[理学—有机化学]