Journal Article10.1021/JO9723063
A novel [3+2] cycloaddition approach to nitrogen heterocycles via phosphine-catalyzed reactions of 2,3-butadienoates or 2-butynoates and dimethyl acetylenedicarboxylate with imines : A convenient synthesis of pentabromopseudilin
Zhenrong Xu,Xiyan Lu +1 more
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Abstract: The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates or 2-butynoates with an appropriate phosphine as the catalyst, toward the electron-deficient imines is described. Triphenylphosphine-catalyzed reaction of methyl 2,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.
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Citations
PPh3-Catalyzed Domino Reaction: A Facile Method for the Synthesis of Chroman Derivatives
TL;DR: A novel domino reaction catalyzed by triphenylphosphine was developed for synthesis of the highly functionalized chroman derivatives and the first example that the gamma-CH(3) of allenoate undergoes cyclization to form chroman derivates was reported.
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A Re(V)-catalyzed C-N bond-forming route to human lipoxygenase inhibitors.
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TL;DR: The ability to couple functionalized components allows for convergent approaches to nitrogen-containing heterocyclic compounds such as the marine antibiotic pentabromopseudilin.
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Unusual [8 + 2] Annelation in the Reactions of Allenic Ester/Ketone-Derived 1,3-Dipoles with Tropone
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