Boc-protected amines via a mild and efficient one-pot Curtius rearrangement |
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Authors: | Lebel Hélène Leogane Olivier |
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Institution: | Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7. helene.lebel@umontreal.ca |
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Abstract: | reaction: see text] 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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