Reactivity of N-(1,2,4-Triazolyl)-Substituted 1,2,3-Triazoles

Reactivity of N-(1,2,4-Triazolyl)-Substituted 1,2,3-Triazoles

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 compoun...

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Veröffentlicht in:Organic letters 2011-09, Vol.13 (18), p.4870-4872
Hauptverfasser: Zibinsky, Mikhail, Fokin, Valery V
Format: Artikel
Sprache:eng
Schlagworte:
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Rhodium - chemistry
Stereoisomerism
Triazoles - chemical synthesis
Triazoles - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201949h