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Palladium‐Catalyzed Arylative Ring‐Opening Reactions of Norbornenols: Entry to Highly Substituted Cyclohexenes, Quinolines, and Tetrahydroquinolines
Author(s) -
Waibel Michael,
Cramer Nicolai
Publication year - 2010
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.201001752
Subject(s) - palladium , aryl , domino , catalysis , chemistry , ring (chemistry) , combinatorial chemistry , organic chemistry , alkyl
Going retro : Palladium‐catalyzed retro‐allylations from norbornene‐derived tertiary alcohols participate in coupling reactions with aryl‐ or vinylhalides to provide tetrasubstituted cyclohexenes with excellent regio‐ and diastereoselectivity (see scheme). This procedure was also exploited in domino reactions to access highly functionalized quinolines and tetrahydroquinolines.