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Synthesis of α‐Ethynyl Glycines
Author(s) -
Bolsakova Jekaterina,
Jirgensons Aigars
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600253
Subject(s) - chemistry , moiety , electrophile , hypervalent molecule , nucleophile , organic chemistry , aminolysis , derivatization , combinatorial chemistry , reagent , high performance liquid chromatography , catalysis
α‐Ethynyl glycine derivatives have a high potential for functionalization by derivatization of the amino acid or acetylene moiety, and, as a result, are important intermediates in the construction of biologically active compounds, including natural products. The main methods for the synthesis of ethynyl glycines and glycinols can be divided into six different transformations: (a) homologations of serinal derivatives, (b) nucleophilic alkynylations of α‐imino esters/alcohols or their precursors α‐halo glycinates, (c) derivatizations of alkynyl imino esters, (d) electrophilic alkynylations of α‐nitro esters and azlactones by using hypervalent iodine reagents, (e) intra‐ and intermolecular aminolysis reactions of epoxides, and (f) propargylic aminations through the cyclization of bis(imidate). This microreview summarizes the methods that were published from 1996 to 2015.