Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.
N,N'-Diphenylguanidinium ion associated with the noncoordinating BArF counterion is shown to be an effective catalyst for the [3,3]-sigmatropic rearrangement of a variety of substituted allyl vinyl ethers. Highly enantioselective catalytic Claisen rearrangements of ester-substituted allyl vinyl ethers are then documented using a new C2-symmetric guanidinium ion derivative.
Uyeda
Christopher
C
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Jacobsen
Eric N
EN
D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D019791:Guanidine / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000498:Allyl Compounds; D004952:Esters; D004987:Ethers; D014753:Vinyl Compounds; C100195:vinyl ether; D019791:Guanidine