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Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles.

ABSTRACT: Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.

SUBMITTER: Zibinsky M

PROVIDER: S-EPMC3224851 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles.

Zibinsky Mikhail M Fokin Valery V VV

Organic letters 20110818 18

Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions w ...[more]

PMID: 21848347

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