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Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.

ABSTRACT: 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.

SUBMITTER: Uyeda C

PROVIDER: S-EPMC2547484 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.

Uyeda Christopher C Jacobsen Eric N EN

Journal of the American Chemical Society 20080625 29

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. ...[more]

PMID: 18576616

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