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Christian Marquis

Bio: Christian Marquis is an academic researcher from University of Neuchâtel. The author has contributed to research in topics: Lewis acids and bases & Thiocyanic acid. The author has an hindex of 1, co-authored 1 publications receiving 17 citations.

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TL;DR: In this paper, a 1,3-dienyl thiocyanic acid ester reacts with acryloyl chloride in presence of Lewis acid catalysts to produce directly the rearranged product of type 3b via a combination of a Diels-Alder reaction with a [3,3] sigmatropic shift; the 1,4-substituted cyclohexene is easily transformed into the 2-azabicyclo[2.2] oct-5-ene derivative 6b, which has been used as precursor for the
Abstract: Buta-1,3-dienyl thiocyanic acid ester reacts with acryloyl chloride in presence of Lewis acid catalysts to produce directly the rearranged product of type 3bvia a combination of a Diels-Alder reaction with a [3,3] sigmatropic shift; the 1,4-substituted cyclohexene is easily transformed into the 2-azabicyclo[2.2.2]oct-5-ene derivative 6b, which has been used as precursor for the synthesis of the Ibogamin skeleton.

17 citations


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TL;DR: This work will attempt to review an area of synthesis that has fascinated us and that the authors find extraordinarily beautiful, namely the combination of catalysis and sigmatropic rearrangements in consecutive and cascade sequences.
Abstract: Catalysis and synthesis are intimately linked in modern organic chemistry. The synthesis of complex molecules is an ever evolving area of science. In many regards, the inherent beauty associated with a synthetic sequence can be linked to a certain combination of the creativity with which a sequence is designed and the overall efficiency with which the ultimate process is performed. In synthesis, as in other endeavors, beauty is very much in the eyes of the beholder.† It is with this in mind that we will attempt to review an area of synthesis that has fascinated us and that we find extraordinarily beautiful, namely the combination of catalysis and sigmatropic rearrangements in consecutive and cascade sequences.

175 citations

Journal ArticleDOI
TL;DR: The key steps to the first asymmetric synthesis involved enantioselective dearomative cyclization of an achiral N-acyl indole that allowed for the efficient construction of the key polycyclic indoline intermediate with a crucial tetrasubstituted stereogenic carbon center.
Abstract: Optically pure hinckdentine A was synthesized on a 300 mg scale via an asymmetric catalysis-based strategy. The key steps to the first asymmetric synthesis involved (i) enantioselective dearomative cyclization of an achiral N-acyl indole that allowed for the efficient construction of the key polycyclic indoline intermediate with a crucial tetrasubstituted stereogenic carbon center, (ii) Beckmann fragmentation-mediated ring expansion, (iii) rearrangement-based introduction of an anilinic nitrogen atom, (iv) regioselective tribromination, and (v) final closure of the cyclic amidine moiety.

96 citations

Journal ArticleDOI
TL;DR: A carboxylate salt is shown to react with an electron-deficient isocyanate to give the corresponding amide in excellent yield at room temperature.

79 citations

Journal ArticleDOI
TL;DR: The application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids, where tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic transformations into other iboga -type alkaloid.

45 citations