Premium
Stereospecific Synthesis of β 3 ‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents
Author(s) -
Temperini Andrea,
Terlizzi Raffaella,
Testaferri Lorenzo,
Tiecco Marcello
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900701
Subject(s) - stereospecificity , chemistry , amine gas treating , oligopeptide , amino acid , combinatorial chemistry , carbon chain , carbon fibers , stereochemistry , coupling reaction , organic chemistry , catalysis , peptide , materials science , biochemistry , composite number , composite material
A stereospecific synthesis of β 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 β‐ and mixed α/β‐oligopeptides without the use of coupling agents.