The iso-Nazarov reaction

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Construction of aryl-substituted triquinanes through the interrupted Nazarov reaction.

The first examples of intermolecular trapping of Nazarov cyclopentenyl cation intermediates by simple arenes to furnish alpha-arylcyclopentanones are described.

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Trimethylaluminum and molecular oxygen are used in tandem to interrupt the Nazarov cyclization. α-Hydroxycyclopentanones are produced in moderate to good yield as a mixture of epimers. This sequence is the first example of combined nucleophilic/electrophilic trapping of the Nazarov oxyallyl intermediate.

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The first calcium-catalysed Nazarov cyclisation is described. The Ca(NTf2)(PF6) complex is found to be a very active catalyst for 4π electrocyclisations. The remarkable catalytic activity of this complex is attributed to its increased Lewis acidity compared to other Ca complexes. Spectroscopic studies have provided an insight into the chelating interactions between the substrate and the Ca cata...

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The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues

The analogous imino-variant of the Nazarov reaction suffers from unfavorable energetics associated with the ring closure process, thereby limiting the utility of this class of reactions. In this report, the realization of the first intermolecular interrupted imino-Nazarov reaction utilizing silylated pyrimidine derivatives as nucleophilic trapping partners culminated in an expedient synthetic r...

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Cyclotomic Nazarov–wenzl Algebras

Nazarov [Naz96] introduced an infinite dimensional algebra, which he called the affine Wenzl algebra, in his study of the Brauer algebras. In this paper we study certain “cyclotomic quotients” of these algebras. We construct the irreducible representations of these algebras in the generic case and use this to show that these algebras are free of rank r(2n − 1)!! (when Ω is u–admissible). We nex...

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ژورنال

عنوان ژورنال: Organic & Biomolecular Chemistry

سال: 2017

ISSN: 1477-0520,1477-0539

DOI: 10.1039/c7ob02220d