Metal-Free Dearomatization: Direct access to Spiroindol(en)ines in Batch and Continuous-Flow.
CHEMISTRY-A EUROPEAN JOURNAL(2019)
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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Key words
dearomatization,flow chemistry,indoles,organocatalysis,spiroindolenine
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