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Published on: April 10, 2019
Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow
Prabhat Ranjan1, Gerardo M Ojeda1,2, Upendra K Sharma1
1Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, Belgium.
Abstract:
A metal-free, phosphine-catalyzed intramolecular "umpolung Michael addition" on alkynes to form spiroindol(en)ines is reported. This nucleophilic catalysis enables the formation of a wide scope of five- and six-membered spiroindol(en)ines in moderate to excellent yields in batch as well as under continuous-flow conditions. Triphenylphosphine-catalyzed nucleophilic activation of alkynes allows the exclusive formation of exo-product under mild reaction conditions.
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