Premium
Domino Reactions Consisting of Heterocyclization and 1,2‐Migration—Redox‐Neutral and Oxidative Transition‐Metal Catalysis
Author(s) -
Umland KlausDaniel,
Palisse Adeline,
Haug Timm T.,
Kirsch Stefan F.
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.201103961
Subject(s) - domino , chemistry , catalysis , redox , oxidative phosphorylation , cascade reaction , bicyclic molecule , transition metal , alkyl , photochemistry , platinum , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry
Two cats, two paths : Two novel domino reactions starting from 6‐hydroxy‐2‐alkyl‐2‐alkynylcyclohexanones have been discovered. While redox‐neutral platinum catalysis gives rise to furans through a sequence of cyclization, 1,2‐shift, and Grob fragmentation, oxidative copper catalysis provides an entry to bicyclic 2,3‐dihydrofurans. Upon cyclization and oxidation, an unusual benzilic acid rearrangement can take place in this case.