Application of Dimedone Enamines as Protecting Groups for Amines and Peptides.

Organic Letters
Sivanna ChithannaDing-Yah Yang

Abstract

A simple protocol for the protection of amines was realized through a base-catalyzed one-pot reaction of dimedone, β-nitroalkene, and amine. Employing this strategy, a variety of amines/amino acids were protected in excellent yields. These acid/base stable protected amines can be deprotected by either ethylene diamine or hydrazine hydrate under mild conditions. The practical application of this orthogonal protecting group was demonstrated by the synthesis of cyclic peptide melanotan II via SPPS.

References

Mar 27, 1998·The Journal of Peptide Research : Official Journal of the American Peptide Society·K AugustynsG Jung
Jan 16, 2002·Journal of Combinatorial Chemistry·David OrainMark Bradley
Oct 9, 2003·The Journal of Peptide Research : Official Journal of the American Peptide Society·P GriecoV J Hruby
Nov 25, 2003·The Journal of Organic Chemistry·Sandra BartoliJeremy D Kilburn
Mar 26, 2004·Organic Letters·Juan Jose Díaz-MochónMark Bradley
May 11, 2004·The Journal of Organic Chemistry·J Nicolás Hernández, Víctor S Martín
Jul 12, 2005·Journal of Combinatorial Chemistry·Christophe PortalMark Bradley
Jun 15, 2006·Chemical Reviews·Patrice RibièreFrédéric Lamaty
Jul 14, 2006·Organic Letters·Sunay V Chankeshwara, Asit K Chakraborti
Apr 15, 2008·Organic Letters·O DemmerH Kessler
Jul 24, 2008·The Journal of Organic Chemistry·Pei-Yu Kuo, Ding-Yah Yang
Apr 15, 2009·Chemical Reviews·Albert Isidro-LlobetFernando Albericio
May 23, 2009·Organic & Biomolecular Chemistry·Trent ConroyRichard J Payne
Jan 16, 2010·Chemistry : a European Journal·Andivelu Ilangovan, Rajendran Ganesh Kumar
Jun 23, 2010·Organic & Biomolecular Chemistry·Trent ConroyRichard J Payne
Oct 1, 2013·The Journal of Organic Chemistry·Amit WaliaRichard B Silverman
Jan 13, 2015·Organic Letters·ThingSoon Jong, Mark Bradley
Apr 15, 2017·The Journal of Organic Chemistry·Michael A SchmidtFrederick Roberts
Apr 24, 2019·Nature Chemistry·Peter R ChristensenBrett A Helms

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