609366-80-5Relevant academic research and scientific papers
o-Boronato- and o-Trifluoroborato - Phosphonium Salts Supported by L-α-Amino Acid Side Chain
Bernard, Julie,Malacea-Kabbara, Raluca,Clemente, Gon?alo S.,Burke, Benjamin P.,Eymin, Marie-Jo?lle,Archibald, Stephen J.,Jugé, Sylvain
, p. 4289 - 4298 (2015/05/13)
(Figure Presented) The synthesis of o-boronato- and o-trifluoroborato-phosphonium salts supported by the l-amino acid side chain is described. The synthesis of these new class of amino acid derivatives was achieved by stereoselective quaternization of o-(
Efficient synthesis of β-halogeno protected L-alanines and their β-phosphonium derivatives
Meyer, Franck,Laaziri, Abdelhamid,Papini, Anna Maria,Uziel, Jacques,Juge, Sylvain
, p. 2229 - 2238 (2007/10/03)
Ring opening of oxazolines, prepared from L-serinates, with trimethylsilyl halides (TMSX) led to β-halogeno-N-benzoyl-α-amino esters in good to excellent yields. Quaternization of triphenylphosphine by the β-bromo or -iodo amino esters gave the corresponding β-phosphonium salts in overall yields of up to 93% and with e.e. >96%. Hydrolysis of the ester function afforded the phosphonium salt bearing an N-benzoyl-α-amino acid substituent, with partial racemization. However, the reaction of the TMSX with the carboxylic salt, prepared by saponification of the starting oxazoline ester, furnished the corresponding β-halogeno-N-benzoyl-α-amino acids in 70-95% yields. Quaternization of triphenylphosphine by the bromo or iodo derivatives led to the phosphonium salts bearing a free acid function in 95% yield, without racemization. The efficiency of this synthesis was demonstrated by the preparation of these phosphonium salts in excellent overall yields, by a one-pot procedure starting from the oxazoline.
