کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5277434 | 1385580 | 2010 | 4 صفحه PDF | دانلود رایگان |
A method for the synthesis of β3-amino acids starting from α-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 β3-amino acids, β3-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into β3-amino acids may not require purification of the intermediate products but a work-up and isolation procedure of crude materials.
A selenium-mediated protocol for the homologation of N-Boc α-amino acids into the corresponding N-phthaloyl β-amino acids has been developed.
Journal: Tetrahedron Letters - Volume 51, Issue 31, 4 August 2010, Pages 4121-4124