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A reasonably stereospecific multistep conversion of Boc-protected alpha-amino acids to Phth-protected beta3-amino acids
A method for the synthesis of beta3-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 beta3-amino acids, beta3-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into beta3-amino acids may not require purification of the intermediate products but a work-up and isolation procedure of crude materials.
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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2384NO – PubChem