Journal
ORGANIC LETTERS
Volume 13, Issue 18, Pages 4870-4872Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201949h
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Funding
- National Institutes of Health, National Institutes of General Medical Sciences [R01-GM087620]
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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.
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