Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.
A novel gold(I)-catalyzed cycloisomerization of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This cascade reaction involves an unprecedented tandem sequence of 1,3- and 1,2-migration of two different migrating groups. It is believed that this transformation likely proceeds via the formation of 1,3-diene intermediate or its precursor, which upon cyclization and aromatization steps transforms into the naphthalene core.
Dudnik
Alexander S
AS
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Schwier
Todd
T
Gevorgyan
Vladimir
V
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D009281:Naphthalenes; D006046:Gold