Premium
Gold(I)‐Catalyzed Synthesis of Functionalized Cyclopentadienes
Author(s) -
Lee Jun Hee,
Toste F. Dean
Publication year - 2007
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.200604006
Subject(s) - regioselectivity , cycloisomerization , chemistry , catalysis , allene , cationic polymerization , intramolecular force , yield (engineering) , medicinal chemistry , homogeneous catalysis , organic chemistry , materials science , metallurgy
. ‥ or a touch of gold : Electrocyclization of the pentadienyl cation produced on coordination of cationic phosphinegold(I) to vinyl allenes results in the regioselective formation of highly functionalized cyclopentadienes. The regioselectivity of the reaction is consistent with an intramolecular 1,2‐hydrogen shift of a gold(I)–carbenoid intermediate (see scheme).