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Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes

Author:
Combee, Logan A., Johnson, Shea L., Laudenschlager, Julie E., Hilinski, Michael K.
Source:
Organic letters 2019 v.21 no.7 pp. 2307-2311
ISSN:
1523-7052
Subject:
acidity, catalysts, chemical structure, cycloaddition reactions, organic compounds, regioselectivity
Abstract:
Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh₂(esp)₂ as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.
Agid:
6363101