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Counteranion-Directed Catalysis in the Tsuji–Trost Reaction: Stereocontrolled Access to 2,5-Disubstituted 3-Hydroxy-Tetrahydrofurans


  • The ICSN and the CNRS are acknowledged for their financial support. Dr. Géraldine Masson (ICSN), Dr. Sylvain Aubry (ICSN), and Dr. Yves Janin (Institut Pasteur, Paris) are warmly acknowledged for valuable scientific discussions.


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Hydrogen bonds can play a prominent role in organometallic catalysis, as shown for the title reaction, in which a counteranion directs the cyclization through the formation of hydrogen bonds that likely involve a proton of the π-allyl/palladium species itself. The reaction allows access to four out of the eight stereoisomers of 2,5-disubstitued 3-hydroxy-tetrahydrofurans and thus fragments of complex natural products.