Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement
2005; American Chemical Society; Volume: 7; Issue: 19 Linguagem: Inglês
10.1021/ol051428b
ISSN1523-7060
Autores Tópico(s)Chemical Synthesis and Reactions
ResumoThe 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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