Premium
Gold‐Catalyzed Rearrangements: Reaction Pathways Using 1‐Alkenyl‐2‐alkynylcyclopropane Substrates
Author(s) -
Barluenga José,
Tudela Eva,
Vicente Rubén,
Ballesteros Alfredo,
Tomás Miguel
Publication year - 2011
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.201007795
Subject(s) - octane , catalysis , chemistry , bicyclic molecule , reactivity (psychology) , cleavage (geology) , ring (chemistry) , bond cleavage , stereochemistry , medicinal chemistry , organic chemistry , materials science , medicine , alternative medicine , pathology , fracture (geology) , composite material
New reactivity patterns : Gold(I) catalyzes the conversion of cyclopentenes ( 1 / 1′ ) into cyclohexadienes ( 2 / 3 ). This profound skeleton rearrangement comprises ring expansion and a [1,2]‐alkynyl shift, and is thought to be initiated by the cleavage of the bridging CC bond. The proposed allyl–gold cation intermediate is trapped with alcohols to provide bicyclo[3.2.1]octadiene and tricyclo[3.2.1.0 2,7 ]octane derivatives.