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Counteranion‐Directed Catalysis in the Tsuji–Trost Reaction: Stereocontrolled Access to 2,5‐Disubstituted 3‐Hydroxy‐Tetrahydrofurans
Author(s) -
Arthuis Martin,
Beaud Rodolphe,
Gandon Vincent,
Roulland Emmanuel
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201205479
Subject(s) - chemistry , catalysis , palladium , reaction conditions , combinatorial chemistry , organometallic chemistry , stereochemistry , organic chemistry
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.