The allylic azide rearrangement: Achieving selectivity

Alina K. Feldman, Benoît Colasson, K. Barry Sharpless, Valery V. Fokin

Research output: Contribution to journalArticlepeer-review

83 Citations (Scopus)


Allylic azides undergo a rapid [3.3]-sigmatropic rearrangement which results in dynamic equilibrium of several isomers. Thus, reactions of allylic azides usually result in mixtures of products. However, even small differences in reactivity of the isomeric allylic azides can be amplified to result in a single product in good to excellent yields. For example, the Cu(I)-catalyzed cycloaddition with alkynes selectively captures primary and secondary allylic azide isomers, whereas MCPBA epoxidation favors isomers which contain more electron-rich double olefins.

Original languageEnglish
Pages (from-to)13444-13445
Number of pages2
JournalJournal of the American Chemical Society
Issue number39
Publication statusPublished - 5 Oct 2005
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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