O-N intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids

The Journal of Organic Chemistry
Mariusz SkwarczynskiYoshiaki Kiso

Abstract

O-N Intramolecular alkoxycarbonyl (carbonate-carbamate) migration was found to occur as a common reaction of hydroxyamino acids under mild basic aqueous conditions with no formation of side products. Carbonate protective groups migrate to produce amino-protected carbamate derivatives of hydroxyamino acids with high efficiency and purity.

References

Sep 2, 1994·Journal of Medicinal Chemistry·S L HarbesonG F Musso
Jul 31, 1998·Journal of Medicinal Chemistry·D J HooverJ L Treadway
Apr 21, 2001·The Journal of Organic Chemistry·S García-Rubio, J Meinwald
Jul 11, 2003·Bioorganic & Medicinal Chemistry Letters·Wieslaw M KazmierskiHanbiao Yang
Oct 14, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·Robert Sheppard
Dec 4, 2003·Bioorganic & Medicinal Chemistry Letters·Mariusz SkwarczynskiYoshiaki Kiso
Oct 21, 2004·Journal of the American Chemical Society·Jennifer M OaksmithBruce Ganem

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Citations

Jul 10, 2008·Journal of Peptide Science : an Official Publication of the European Peptide Society·Taku YoshiyaYoshiaki Kiso
Dec 5, 2012·Chemical Biology & Drug Design·Bahaa El-Dien M El-GendyAlan R Katritzky
Jan 21, 2017·Organic & Biomolecular Chemistry·Mathieu EsgulianDavid J Aitken
Feb 23, 2013·Organic & Biomolecular Chemistry·Waleed M HusseinMariusz Skwarczynski

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