Affiliation:
1. Université Paris-Saclay CNRS Institut de Chimie des Substances Naturelles UPR2301 91198 Gif-sur-Yvette France
2. INSA Rouen Normandie Univ Rouen Normandie CNRS Normandie Univ COBRA UMR 6014 F-76000 Rouen France
Abstract
AbstractA strategy to access fluorinated spiroindolenines has been developed, involving a selective functionalization of indoles with fluorinated moieties and subsequent catalytic dearomatization. Trifluomethylthio (SCF3), diethyl phosphono(difluoromethyl)thio (SCF2P(O)(OEt)2) and (phenylsulfonyl)difluoromethyl (CF2SO2Ph) groups were embedded at the C2 position of indole derivatives substituted with alkynes, allenes, and allyl carbonate moieties at the C3 position. A gold‐catalyzed cycloisomerization gave access to five spiroindolenines, and an enantioselective palladium catalyzed cyclization provided 10 fluorinated spirocyclic products with up to 77% ee.