Display options
Cite
Goudedranche S, Besnard C, Egger L, et al. Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams. Angew Chem Int Ed Engl. 2016;55(44):13775-13779doi: 10.1002/anie.201607574.
Goudedranche, S., Besnard, C., Egger, L., & Lacour, J. (2016). Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams. Angewandte Chemie (International ed. in English), 55(44), 13775-13779. https://doi.org/10.1002/anie.201607574
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." Angewandte Chemie (International ed. in English) vol. 55,44 (2016): 13775-13779. doi: https://doi.org/10.1002/anie.201607574
Goudedranche S, Besnard C, Egger L, Lacour J. Synthesis of Pyrrolidines and Pyrrolizidines with α-Pseudoquaternary Centers by Copper-Catalyzed Condensation of α-Diazodicarbonyl Compounds and Aryl γ-Lactams. Angew Chem Int Ed Engl. 2016 Oct 24;55(44):13775-13779. doi: 10.1002/anie.201607574. Epub 2016 Oct 04. PMID: 27701808.
Copy Download .nbib Format: NLM
Share it on

Angew Chem Int Ed Engl. 2016 Oct 24;55(44):13775-13779. doi: 10.1002/anie.201607574. Epub 2016 Oct 04.

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

Angewandte Chemie (International ed. in English)

Sébastien Goudedranche, Céline Besnard, Léo Egger, Jérôme Lacour

Affiliations

  1. Département de Chimie Organique, Université de Genève, quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland.
  2. Laboratoire de Cristallographie, Université de Genève, quai Ernest Ansermet 24, 1211, Geneva 4, Switzerland.
  3. Département de Chimie Organique, Université de Genève, quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland. [email protected].

PMID: 27701808 DOI: 10.1002/anie.201607574

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).

© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: acyl migrations; diazo reagents; pyrrolidines; pyrrolizidines; γ-lactams

Publication Types