Modular Hemisyntheses of Boronato- and Trifluoroborato-SubstitutedL-NHBoc Amino Acid and Peptide Derivatives
Modular hemisyntheses of boronato- and trifluoroborato-substituted amino acid and peptide derivatives by using Wittig and C–H iridium-catalyzed borylation as key reactions, are described. Amino ester precursors bearing an aromatic moiety on a lateral chain were prepared by reaction of a new L-NHBoc-amino acid Wittig reagent with the corresponding aromatic aldehydes. After esterification and hydrogenation, the borylation of amino esters was achieved with yields up to 82 % by using the catalysed reaction of bis(pinacolato) diborane reagent (B2Pin2) in the presence of an iridium complex. Interestingly, this iridium-catalyzed borylation was also performed with a dipeptide in 78 % yield. Finally…
ChemInform Abstract: Efficient Stereoselective Synthesis of Boron L-amino Acid Derivatives Using Wittig and Borylation Reactions
The stereoselective synthesis of a new classes of boronato- or trifluoroborato aminoacids and peptides was described using Wittig and C-H iridium borylation as key reactions. A trifluoroborato-thio...
Efficient Stereoselective Synthesis of Boron L-Amino Acid Derivatives Using Wittig and Borylation Reactions
The stereoselective synthesis of a new classes of boronato- or trifluoroborato aminoacids and peptides was described using Wittig and C-H iridium borylation as key reactions. A trifluoroborato-thio...
ChemInform Abstract: Modular Hemisyntheses of Boronato- and Trifluoroborato-Substituted L-NHBoc Amino Acid and Peptide Derivatives.
Modular hemisyntheses of boronato- and trifluoroborato-substituted amino acid derivatives are achieved based on the reaction of Wittig reagent (I) with aldehydes followed by Ir-catalyzed boronation.
Designing Silylatedl-Amino Acids using a Wittig Strategy: Synthesis of Peptide Derivatives and18F-Labelling
An efficient semisynthesis of silylated l-amino acids by reaction of silylated benzaldehydes with a phosphonium l-amino acid used as a Wittig reagent is described. The efficiency of the silylated l-amino acids in peptide synthesis was investigated by coupling both the carboxylic acid and the amino moiety with l-alanine and phenylalanine derivatives, respectively. The silylated derivatives were treated with KF or tetrabutylammonium fluoride to give the corresponding fluorosilyl derivatives without racemization. The hydrolysis of the fluorosilylated derivatives in phosphate buffer at pH 7.2 was checked. Finally, the 18F-labelling of di-tert-butylsilylated saturated and unsaturated dipeptides …