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Synthesis of Chiral β3-Aminoxy Peptides

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journal contribution
posted on 29.10.2004, 00:00 by Dan Yang, Yu-Hui Zhang, Bing Li, Dan-Wei Zhang
A series of chiral β3-aminoxy acids or amides with various side chains have been synthesized via two different approaches. One is the Arndt−Eistert homologation approach, using chiral α-aminoxy acids as starting materials. The other approach, utilizing the enantioselective reduction of β-keto esters catalyzed by baker's yeast or chiral Ru(II) complexes, produces chiral β3-aminoxy acids with nonproteinaceous side chains. The oligomers of β3-aminoxy acids can be readily prepared using EDCI/HOAt as the coupling reagent.