Asymmetric synthesis of medium-sized rings by intramolecular Au(I)-catalyzed cyclopropanation.
An efficient method for the asymmetric gold(I)-catalyzed preparation of medium sized rings has been developed. The method provides 7- to 9-membered rings in excellent yield. High enantioselectivities can be achieved for 7- and 8-membered ring products employing chiral gold(I) complexes. The results provide insight into the mechanism, showing the fluxional nature of gold(I)-stabilized vinyl carbenoid intermediates.
Watson
Iain D G
ID
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Ritter
Stefanie
S
Toste
F Dean
FD
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis*; D034242:Cyclooctanes / Q000138:chemical synthesis*; D003521:Cyclopropanes / Q000138:chemical synthesis*; D006046:Gold / Q000737:chemistry
D000480:Alkynes; D003508:Cycloheptanes; D034242:Cyclooctanes; D003521:Cyclopropanes; D006046:Gold