A reasonably stereospecific multistep conversion of Boc-protected alpha-amino acids to Phth-protected beta(3)-amino acids

作者：Temperini Andrea^*; Capperucci Antonella; Degl'Innocenti Alessandro; Terlizzi Raffaella; Tiecco Marcello

来源：Tetrahedron Letters, 2010, 51(31): 4121-4124.

DOI：10.1016/j.tetlet.2010.05.143

• alpha-Amino acids
• Selenium
• Propargylic amines
• beta-Amino acids

A method for the synthesis of beta(3)-amino acids starting from alpha-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed 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 beta(3)-amino acids, beta(3)-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into beta(3)-amino acids may not require purification of the intermediate products but a workup and isolation procedure of crude materials.

• 出版日期2010-8-4