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Dual vicinal functionalisation of heterocycles via an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.

ABSTRACT: A dual vicinal functionalisation cascade involving the union of heterocycles and allyl sulfoxides is described. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important C3 thio, C2 carbo substituted indoles. The reaction operates under mild, metal free conditions and without directing groups, via an interrupted Pummerer coupling of activated allyl sulfoxides, generating allyl heteroaryl sulfonium salts that are predisposed to a charge accelerated [3,3]-sigmatropic rearrangement.

SUBMITTER: Siauciulis M

PROVIDER: S-EPMC5870476 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Dual vicinal functionalisation of heterocycles <i>via</i> an interrupted Pummerer coupling/[3,3]-sigmatropic rearrangement cascade.

Šiaučiulis Mindaugas M Sapmaz Selma S Pulis Alexander P AP Procter David J DJ

Chemical science 20171117 3

A dual vicinal functionalisation cascade involving the union of heterocycles and allyl sulfoxides is described. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important C3 thio, C2 carbo substituted indoles. The reaction operates under mild, metal free conditions and without directing groups, <i>via</i> an interrupted Pummerer coupling of activated allyl sulfoxides, generating allyl heteroaryl sulfonium salts that are predisposed to a ch ...[more]

PMID: 29629145

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