Ethynylglycine synthon from Garner's aldehyde: a useful precursor for the synthesis of non-natural amino acids

Abstract : The ethynylglycine synthon, namely (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyl-oxazolidine, can be obtained through the synthetic elaboration of naturally occurring serine. This compound has been exploited as a helpful and versatile non-racemic building block to be used for the design and synthesis of biologically important compounds, mainly non-natural-amino acids. Taking advantage of the terminal acetylene moiety several synthetic applications can be designed. Metalation followed by trapping with electrophiles or Cu=Pd catalysed coupling with aromatic halogenides are shown to deliver useful precursors of ethynylglycine derivatives. Additions of bimetallic reagents like stannyl-or silylcuprates are useful entries for the regio-and stereoselective functionalization of the lateral chain, aimed at the synthesis of modified vinylglycine precursors. An overview of our recent work in the field will be given, and the use of ethynylglycine synthon in the synthesis of non-racemic saturated and unsaturated non-natural amino acids will be briefly reviewed.
Document type :
Journal articles
Liste complète des métadonnées

https://hal.archives-ouvertes.fr/hal-02002665
Contributor : Patrick Meffre <>
Submitted on : Monday, February 11, 2019 - 5:57:33 PM
Last modification on : Monday, February 11, 2019 - 7:06:13 PM

File

Reginato_Meffre_AA_05_HAL_2.pd...
Files produced by the author(s)

Identifiers

Citation

G. Reginato, P. Meffre, F. Gaggini. Ethynylglycine synthon from Garner's aldehyde: a useful precursor for the synthesis of non-natural amino acids. Amino Acids, Springer Verlag, 2005, 29 (2), pp.81-87. 〈10.1007/s00726-005-0184-y〉. 〈hal-02002665〉

Share

Metrics

Record views

38

Files downloads

14