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Synthesis of Polyconjugated Bis-Enones Through a Gold-Catalyzed 1,3-Acyloxy Migration-Cyclization-1,5-Acyl Shift Cascade Reaction

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Gold-Catalyzed Cycloisomerization Reactions Through Activation of Alkynes

Part of the book series: Springer Theses ((Springer Theses))

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Abstract

The following part will deal with a new reaction we designed in our laboratory. Initial gold catalyzed rearrangement into an allenyl ester triggers a series of elementary steps to fully rearrange the starting material. Before the results being presented and discussed, we will shortly introduce the reactivities accessible from allenyl esters upon gold catalysis and focus on their use in allenyne-type cycloisomerizations.

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Notes

  1. 1.

    To the best of our knowledge, the only example of nucleophilic attack at the central carbon atom of the allenyl ester was reported in the hydration of α-acyloxy-α-alkynyl silanes, thanks to the β-silicon effect, see: [10].

  2. 2.

    Selected examples, O-nucleophiles [11, 12], N-nucleophiles [13], C-nucleophiles [14, 15].

  3. 3.

    Selected examples, [2 + 2] [16], [3 + 2] [17], [4 + 3] [18, 19], Nazarov [20].

  4. 4.

    For intramolecular trapping of this carbene with double bonds in the metala-Nazarov reaction of vinyl allenyl esters, see: [21, 22].

  5. 5.

    Mo-mediated carbonylation of allenyl arene-ynes gave by-products derived from the Myers-Saito rearrangement, see [26].

  6. 6.

    For seminal works on the Myers-Saito rearrangement, see [27, 28].

  7. 7.

    Comparable intermediates were invoked in the intramolecular Diels-Alder reaction of dienynes, see [31].

  8. 8.

    Selected reviews: [37–41].

  9. 9.

    For recent reviews on Nazarov cyclization, see [47–50].

  10. 10.

    According to 1H, 13C NMR and mass spectrometry.

  11. 11.

    See Ref. [57] and also [58–60].

  12. 12.

    In previous tests with 2 mol% of the catalyst, the conversion was blocked at about 50 %.

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  1. Paris Institute of Molecular Chemistry, University Pierre and Marie Curie, Paris, France

    Antoine Simonneau

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  1. Antoine Simonneau
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Correspondence to Antoine Simonneau .

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Simonneau, A. (2014). Synthesis of Polyconjugated Bis-Enones Through a Gold-Catalyzed 1,3-Acyloxy Migration-Cyclization-1,5-Acyl Shift Cascade Reaction. In: Gold-Catalyzed Cycloisomerization Reactions Through Activation of Alkynes. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-06707-0_3

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