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.
Counteranion-Directed Catalysis in the Tsuji–Trost Reaction: Stereocontrolled Access to 2,5-Disubstituted 3-Hydroxy-Tetrahydrofurans†
Article first published online: 20 SEP 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 42, pages 10510–10514, October 15, 2012
How to Cite
Arthuis, M., Beaud, R., Gandon, V. and Roulland, E. (2012), Counteranion-Directed Catalysis in the Tsuji–Trost Reaction: Stereocontrolled Access to 2,5-Disubstituted 3-Hydroxy-Tetrahydrofurans . Angew. Chem. Int. Ed., 51: 10510–10514. doi: 10.1002/anie.201205479
- Issue published online: 10 OCT 2012
- Article first published online: 20 SEP 2012
- Manuscript Received: 11 JUL 2012
- counteranion-directed catalysis;
- hydrogen bonds;
- natural products;
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.