The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses

Organic & Biomolecular Chemistry
Arun K GhoshMargherita Brindisi

Abstract

The Curtius rearrangement is a versatile reaction in which a carboxylic acid can be converted to an isocyanate through an acyl azide intermediate under mild conditions. The resulting stable isocyanate can then be readily transformed into a variety of amines and amine derivatives including urethanes and ureas. There have been wide-ranging applications of the Curtius rearrangement in the synthesis of natural products and their derivatives. Also, this reaction has been extensively utilized in the synthesis and application of a variety of biomolecules. In this review, we present mechanistic studies, chemical methodologies and reagents for the synthesis of isocyanates from carboxylic acids, the conversion of isocyanates to amines and amine derivatives, and their applications in the synthesis of bioactive natural products and their congeners.

References

Apr 13, 1977·Journal of the American Chemical Society·H TaninoY Kishi
Feb 7, 2001·Organic Letters·W R Roush, L A Pfeifer
Aug 17, 2001·Organic Letters·A K GhoshJ Cappiello
Sep 6, 1996·The Journal of Organic Chemistry·Arun K. Ghosh, Wenming Liu
Dec 6, 2001·Journal of the American Chemical Society·A B SmithR M Corbett
Aug 17, 2002·The Journal of Organic Chemistry·Sanjita SasmalMartin E Maier
Sep 13, 2002·Journal of the American Chemical Society·Amos B SmithR Michael Corbett
Mar 27, 2003·Chemistry : a European Journal·Lubov S KlimenkoNina P Gritsan
Sep 27, 2003·The Journal of Organic Chemistry·Jason A MillerSonBinh T Nguyen
Nov 25, 2003·The Journal of Organic Chemistry·Lavinia MarinescuMikael Bols
Feb 28, 2004·Organic Letters·Patrick D O'ConnorMatthew M W McLachlan
Jul 29, 2005·Organic Letters·James A MacKayViresh H Rawal
Aug 16, 2005·Angewandte Chemie·Stefan BräseViktor Zimmermann
Sep 9, 2005·Organic Letters·Hélène Lebel, Olivier Leogane
Feb 24, 2006·Organic Letters·Natsuko KagawaMasahiro Toyota
Jul 14, 2006·Organic Letters·Kelly A Fairweather, Lewis N Mander
Jul 25, 2007·Angewandte Chemie·John C Jewett, Viresh H Rawal
Oct 4, 2007·The Journal of Organic Chemistry·Bryan K Chan, Marco A Ciufolini
Dec 18, 2007·Organic Letters·Toshiyuki KanTohru Fukuyama
Apr 19, 2008·Organic & Biomolecular Chemistry·Marcus BaumannJason P Tierney
Oct 1, 1948·Chemical Reviews·J H SAUNDERS, R J SLOCOMBE
Aug 13, 2009·Organic Letters·Michael T CrimminsGregory M Schaaf
Oct 31, 2009·Organic Letters·Takahiro KoshibaTohru Fukuyama
Sep 30, 2010·Chemical Society Reviews·Yoann AubinJean-Luc Renaud
Jan 14, 2011·Bioorganic & Medicinal Chemistry·Daisuke OgasawaraNaoki Miyata
Apr 21, 2011·Journal of Medicinal Chemistry·Stephen D Roughley, Allan M Jordan
Aug 31, 2011·Organic Letters·Weili Zhao, Erick M Carreira
Oct 20, 2011·Organic Letters·Kiri StevensJeremy Robertson
Dec 21, 2012·Organic Letters·Yong-Geun JungCheon-Gyu Cho
Apr 24, 2013·Angewandte Chemie·Frauke Messik, Markus Oberthür

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Citations

Dec 5, 2018·Chemistry : a European Journal·Grant B FrostChristopher J Douglas
Apr 11, 2019·Organic & Biomolecular Chemistry·Angela S Carlson, Joseph J Topczewski
Jul 18, 2020·Organic & Biomolecular Chemistry·Kaushik ChakrabartiSabuj Kundu
Oct 1, 2020·Chemistry : a European Journal·Simon N SmithStephen J Connon
Aug 7, 2020·Chemical Communications : Chem Comm·Ignacio D LemirJuan C Scaiano
Sep 19, 2020·Organic & Biomolecular Chemistry·Karoline G PrimdahlMarius Aursnes
Jul 16, 2020·Chemistry : a European Journal·Rosa López, Claudio Palomo
Aug 3, 2021·Journal of the American Chemical Society·Pei Qu, Scott A Snyder
Jul 16, 2020·The Journal of Physical Chemistry. a·Sumitra GodaraManikandan Paranjothy
Dec 4, 2019·Journal of Medicinal Chemistry·Arun K Ghosh, Margherita Brindisi

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