Metal-Free Dearomatization: Direct Access to Spiroindol(en)ines in Batch and Continuous-Flow

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. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Авторы
Ranjan P.1 , Ojeda G.M.1, 2 , Sharma U.K.1 , Van Der Eycken E.V.
Журнал
Chemistry - A European Journal
Издательство
Wiley-VCH Verlag
Язык
Английский
Статус
Опубликовано
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DOI
10.1002/CHEM.201805945
Год
2019
Организации
  • 1 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 2 Center for Natural Products Research, Faculty of Chemistry, University of Havana, ZapatayG, Havana, 10400, Cuba
  • 3 People's Friendship University of Russia, RUDN University), Miklukho -Maklaya street 6, Moscow, 117198, Russian Federation
Ключевые слова
dearomatization; flow chemistry; indoles; organocatalysis; spiroindolenine
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