title: Counteranion-directed catalysis in the Tsuji-Trost reaction: stereocontrolled access to 2,5-disubstituted 3-hydroxy-tetrahydrofurans.
abstract: 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.
authors.affiliation: CNRS/Institut de Chimie des Substances Naturelles (ICSN), Centre de Recherche de Gif, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Martin
authors.initials: M
authors.lastname: Arthuis
authors.forename: Rodolphe
authors.initials: R
authors.lastname: Beaud
authors.forename: Vincent
authors.initials: V
authors.lastname: Gandon
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Roulland
mesh_terms: D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D005663:Furans; D010165:Palladium