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Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams

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Published in Angewandte Chemie: International Edition. 2016, vol. 55, no. 44, p. 13775-13779
Abstract N-aryl γ-lactams react intermolecularly with acceptor–acceptor diazo reagents, usually dicarbonyl compounds, in a copper-catalyzed process to yield functionalized pyrrolidines with α-pseudoquaternary centers. As 1,2-acyl or -phosphoryl migration is preferred, single regioisomers are obtained. Furthermore, in the presence of a Lewis acid, subsequent Friedel–Crafts reactions yield tricyclic pyrrolizidines in excellent yields (90–96 %) and diastereoselectivities (up to >20:1).
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Other version: http://doi.wiley.com/10.1002/anie.201607574
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Research group Groupe Lacour
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GOUDEDRANCHE, Sébastien et al. Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams. In: Angewandte Chemie: International Edition, 2016, vol. 55, n° 44, p. 13775-13779. https://archive-ouverte.unige.ch/unige:88396

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Deposited on : 2016-10-24

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