NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups

Jon C. Loren, Antoni Krasiński, Valery V. Fokin, K. Barry Sharpless

Research output: Contribution to journal › Article

Abstract

NH-1,2,3-triazoles have been prepared via the copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and three N-protected organic azides, azidomethyl pivalate, azidomethyl morpholine-4-carboxylate, and azidomethyl N,N-diethylcarbarnate. These organic azides were easily prepared on 0.1-mol scale in one or two steps from inexpensive commercially available materials. The cleaving properties of N-substituents in the resulting 1,2,3-triazole products with aqueous sodium hydroxide vary from

Original language	English
Article number	Y06505ST
Pages (from-to)	2847-2850
Number of pages	4
Journal	Synlett
Issue number	18
DOIs	https://doi.org/10.1055/s-2005-918944
Publication status	Published - 3 Nov 2005
Externally published	Yes

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Keywords

Alkynes
Azides
Click chemistry
Cycloaddition
Heterocycles
Protecting groups
Triazoles

ASJC Scopus subject areas

Organic Chemistry

Cite this

Loren, J. C., Krasiński, A., Fokin, V. V., & Sharpless, K. B. (2005). NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups. Synlett, (18), 2847-2850. [Y06505ST]. https://doi.org/10.1055/s-2005-918944

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AU - Sharpless, K. Barry

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10.1055/s-2005-918944