Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement

Hélène Lebel* and Olivier Leogane
Dpartement de chimie, Universit de Montral, P.O. Box 6128, Station Downtown, Montral, Qubec, Canada H3C 3J7
Org. Lett., 2005, 7 (19), pp 4107–4110
DOI: 10.1021/ol051428b
Publication Date (Web): August 19, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, helene.lebel@umontreal.ca

Abstract

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The reaction of a carboxylic acid with di-tert-butyl dicarbonate and sodium azide allowed the formation of an acyl azide intermediate, which undergoes a Curtius rearrangement in the presence of tetrabutylammonium bromide and zinc(II) triflate. The trapping of the isocyanate derivative in the reaction mixture led to the desired tert-butyl carbamate in high yields at low temperature. These reaction conditions are compatible with a variety of substrates, including malonate derivatives, which provide access to protected amino acids.

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History

  • Published In Issue September 15, 2005
  • Received June 20, 2005

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