Raffaella Terlizzi

Additive-Free Chemoselective Acylation of Amines

Aliphatic and aromatic amines are efficiently acylated by acetic, pivalic, benzoic, phthalic, or maleic anhydrides in ethyl acetate at room temperature. Under the same experimental conditions, amino alcohols are chemoselectively acylated at the amino group.

Stereospecific Synthesis of β3‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents

A stereospecific synthesis of beta(3)-amino acids has been accomplished starting from readily available and enantioenriched propargylic alcohols. This conversion can be effected in only three steps by selenium-mediated organic transformations of the carbon-carbon triple bond. This method is especially attractive because the reactive Se-phenyl selenocarboxylate intermediates can be trapped with the amine functionality of an amino acid derivative. Through this strategy a chain elongation at the N-terminus has been effected. The N-deprotection and repetition of the homologation with other Se-phenyl selenocarboxylate intermediates produced beta- and mixed alpha/beta-oligopeptides without the use of coupling agents.

Novel Stereoselective Synthesis of (R)-3-Aminotetradecanoic Acid (Iturinic Acid)

(R)-3-Aminotetradecanoic acid (iturinic acid) has been synthesized starting from dodecanoyl chloride. This new synthetic approach involved the enantioselective reduction of an ynone to the corresponding propargylic alcohol and then into a protected propargylic amine. The iturinic acid was obtained by the transformation of a (phenylseleno)acetylene intermediate into a carboxylic group followed by N-deprotection.

Stereoselective Synthesis of β3-Amino Acids and β-Oligopeptides Promoted by Organoselenium Intermediates

Abstract Propargylic amines can be valid precursors for the synthesis of β3-amino acids. This can be effected by a selenium-mediated conversion of the carbon–carbon triple bond to a, Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols, or the amine of an amino acid derivative to give β3-amino acids, β3-amino esters, or mixed peptides, respectively.