Journal ArticleDOI
Lewis-acid catalysed tandem reaction Diels–Alder–[3,3] sigmatropic shift between buta-1,3-dienyl thiocyanic acid ester and acryloyl chloride: application in the synthesis of 2-azabicyclo[2.2.2]oct-5-ene derivatives
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TLDR
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 theAbstract:
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.read more
Citations
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Toward a Symphony of Reactivity: Cascades Involving Catalysis and Sigmatropic Rearrangements
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.
Journal ArticleDOI
Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach
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.
Journal ArticleDOI
Reaction of Thioacids with Isocyanates and Isothiocyanates: A Convenient Amide Ligation Process
David Crich,Kaname Sasaki +1 more
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.
Journal ArticleDOI
Bis hin zu einer Symphonie der Reaktivität: Kaskaden mit Katalysen und sigmatropen Umlagerungen
Journal ArticleDOI
Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids
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.
References
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Journal ArticleDOI
Sequential Transformations in Organic Chemistry: A Synthetic Strategy with a Future†
Lutz F. Tietze,Uwe Beifuss +1 more
TL;DR: Organic-chemical synthesis has always fascinated chemists and will not lose its importance in the future as mentioned in this paper, and it is a truism that all chemists are dependent on the synthesis of those compounds with which they want to work.
Journal ArticleDOI
Sequentielle Transformationen in der Organischen Chemie eine Synthesestrategie mit Zukunft
Lutz F. Tietze,Uwe Beifuss +1 more
TL;DR: The organisch-chemische Synthese hat stets eine grose Faszination auf den Chemiker ausgeubt, und sie wird auch in Zukunft nichts von ihrer Bedeutung verlieren as discussed by the authors.
Book
Tandem organic reactions
TL;DR: Aldol Condensation as discussed by the authors is a cycloaddition of Alkenes and Alkynes, and it can be expressed as a pair of Vicinal Difunctionalization of Alknes and alkynes.
Journal ArticleDOI
A total synthesis of racemic and optically active ibogamine. Utilization and mechanism of a new silver ion assisted palladium catalyzed cyclization
Journal ArticleDOI
Steric steering with supported palladium catalysts
Barry M. Trost,Ehud Keinan +1 more
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