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Reagent-controlled regiodivergence in the [3,3]-sigmatropic rearrangement of N-(acyloxy)enamides

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Abstract

A regiodivergent [3,3]-sigmatropic rearrangement of N-(acyloxy)enamides has been developed. The regioselectivity of the rearrangement based on the N–O bond cleavage was complementarily controlled by changing reaction conditions. The treatment of enamides with LiHMDS afforded enamido carboxylic acid via C–C bond formation, while the reaction with 2,4,6-collidine under thermal conditions afforded an enamido ester via C–O bond formation.

Graphical abstract: Reagent-controlled regiodivergence in the [3,3]-sigmatropic rearrangement of N-(acyloxy)enamides

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Publication details

The article was received on 07 Sep 2019, accepted on 25 Sep 2019 and first published on 27 Sep 2019


Article type: Research Article
DOI: 10.1039/C9QO01109A
Org. Chem. Front., 2019, Advance Article

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    Reagent-controlled regiodivergence in the [3,3]-sigmatropic rearrangement of N-(acyloxy)enamides

    N. Takeda, N. Arisawa, M. Miyamoto, Y. Kobori, T. Shinada, O. Miyata and M. Ueda, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01109A

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