118525-58-9Relevant academic research and scientific papers
Novel Modifications of Peptides: Simple Syntheses of Difunctionalized Enamines, Enol Ethers, and Thioenol Ethers from Carboxylic Acids via Acylimidazole and Enol Phosphate Intermediates
Sauve, Gilles,Berre, Nicolas Le,Zacharie, Boulos
, p. 3002 - 3004 (2007/10/02)
The condensation of carboxylic acids 5 (N-protected amino acids or dipeptides) and active methylene compounds to give difunctionalized enols 6 is accomplished by the use of 1,1'-carbonyldiimidazole as an activating reagent.Enamines 7a, enol ethers 7b, and thioenol ethers 7c are obtained directly from the corresponding nucleophiles and the intermediates formed from enols 6 by the action of phenyl phosphorodichloridate.The integrity of peptide chiral centers is maintained during these transformations.
CARBOXYL-MODIFIED AMINO ACIDS AND PEPTIDES: II) A CONVENIENT ROUTE FOR THE SYNTHESIS OF DIFUNCTIONALIZED ENAMINES FROM THIOAMIDES VIA THIOIMINIUM SALTS
Sauve, Gilles,Berre, Nicolas Le,Zacharie, Boulos
, p. 2299 - 2302 (2007/10/02)
From thioamides 4, via thioiminium salts 5, various difunctionalized enamines 6 with different electron-withdrawing groups E, E' (E: CN, CO2Me, COR, SO2R, etc; E': CN, CO2Me) are prepared.Application of the methodology, the determination of stereochemistry and degree of racemization of some amino acids are discussed.
