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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 19
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Original Articles

Synthesis of Hydroxymethyl Side-Chained α-Aminoxy Diamide

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Pages 2815-2821 | Received 27 Mar 2009, Published online: 25 Aug 2010

REFERENCES

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  • For selective reviews on foldamers, see (a) Seebach , D. ; Matthews , J. L. β-Peptides: A surprise at every turn . Chem. Commun. 1997 , 2015 – 2022 ; (b) Gellman , S. H. Foldamers: A manifesto . Acc. Chem. Res. 1998 , 31 , 173 – 180 .
  • For a review on aminoxy peptides, see Li , X. ; Yang , D. Peptides of aminoxy acids as foldamers . Chem. Commun. 2006 , 3367 – 3379 , and references cited therein .
  • Li , X. ; Wu , Y.-D. ; Yang , D. α-Aminoxy acids: New possibilities from foldamers to anion receptors and channels . Acc. Chem. Res. 2008 , 41 , 1428 – 1438 , and references cited therein .
  • (a) Shin , I. ; Lee , M. ; Lee , J. ; Jung , M. ; Lee , W. ; Yoon , J. Synthesis of optically active phthaloyl D-aminooxy acids from L-amino acids or L-hydroxy acids as building blocks for the preparation of aminooxy peptides . J. Org. Chem. 2000 , 65 , 7667 – 7675 ; (b) Yang , D. ; Li , B. ; Ng , F.-F. ; Yan , Y.-L. ; Qu , J. ; Wu , Y.-D. Synthesis and characterization of chiral N‒O turns induced by α-aminoxy acids . J. Org. Chem. 2001 , 66 , 7303 – 7312 ; (c) Yamawaki , K. ; Nomura , T. ; Yasukata , T. ; Uotani , K. ; Miwa , H. ; Takeda , K. ; Nishitani , Y. A novel series of parenteral cephalosporins exhibiting potent activities against Pseudomonas aeruginosa and other Gram-negative pathogens: Synthesis and structure–activity relationships . Bioorg. Med. Chem. 2007 , 15 , 6716 – 6732 .
  • Pirrung , M. C. ; Brown , W. L. Diazotization of 1-aminocyclopropanecarboxylic acid: Solution chemistry of oxaspiropentanone. J. Am. Chem. Soc. 1990, 112, 6388–6389.

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