Synfacts 2007(9): 0953-0953  
DOI: 10.1055/s-2007-968844
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Mediated Nazarov Cyclization/1,2-Sigmatropic Rearrangement

Contributor(s): Mark Lautens, Praew Thansandote
J. Huang, A. J. Frontier*
University of Rochester, USA
Further Information

Publication History

Publication Date:
23 August 2007 (online)


A stereoselective copper-mediated Nazarov cyclization/Wagner-Meerwein rearrangement produces two types of five-membered spirocyclic products depending on the substrate. Substrates containing a cinnamyl substituent lead to products where the substituent migrates after the Nazarov cyclization, whereas substrates with an alkyl substituent undergo hydrogen migration after cyclization. Six-membered spirocycles can also be formed from the corresponding seven-membered-ring starting material. The enantioselectivities for the reaction are low, but unoptimized.